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[ CAS No. 120-35-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 120-35-4
Chemical Structure| 120-35-4
Chemical Structure| 120-35-4
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Product Details of [ 120-35-4 ]

CAS No. :120-35-4 MDL No. :MFCD00017166
Formula : C14H14N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :LHMQDVIHBXWNII-UHFFFAOYSA-N
M.W : 242.27 Pubchem ID :8426
Synonyms :

Calculated chemistry of [ 120-35-4 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.07
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 71.55
TPSA : 64.35 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.07
Log Po/w (XLOGP3) : 2.05
Log Po/w (WLOGP) : 2.35
Log Po/w (MLOGP) : 2.08
Log Po/w (SILICOS-IT) : 1.89
Consensus Log Po/w : 2.09

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.86
Solubility : 0.332 mg/ml ; 0.00137 mol/l
Class : Soluble
Log S (Ali) : -3.03
Solubility : 0.226 mg/ml ; 0.000934 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.69
Solubility : 0.00495 mg/ml ; 0.0000204 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.58

Safety of [ 120-35-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 120-35-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 120-35-4 ]

[ 120-35-4 ] Synthesis Path-Downstream   1~93

  • 1
  • [ 120-35-4 ]
  • [ 94-05-3 ]
  • <(2-Methoxy-5-phenylcarbamoyl-anilino)-methylen>-cyanessigsaeureethylester [ No CAS ]
  • 2
  • [ 120-35-4 ]
  • [ 603-33-8 ]
  • [ 228422-87-5 ]
YieldReaction ConditionsOperation in experiment
With triethylamine;copper diacetate; In dichloromethane; Example 28 4-Methoxy-3-phenylamino-N-phenyl-benzamide Prepared according to the procedure of Example 25 using 3-amino-4-methoxy-N-phenyl-benzamide (1.5 g, 6.2 mmol), triphenylbismuth (2.9 g, 6.6 mmol), copper(II) acetate (1.13 g, 6.2 mmol), and triethylamine (0.62 g, 6.2 mmol) to give a solid which was recrystallized from ethanol then subjected to chromatography on a column of silica gel in dichloromethane to afford the product (0.8 g); m.p. 194-195 C. after an additional recrystallization from ethyl alcohol. Calculated for C20H18N2O2: C, 75.45; H, 5.70; N, 8.80. Found: C, 74.66; H, 5.43; N, 8.67.
  • 3
  • [ 120-35-4 ]
  • [ 83724-41-8 ]
  • 3-(2-methoxy-phenylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine;copper diacetate; Example 29 3-(2-Methoxy-phenylamino)-4-methoxy-N-phenyl-benzamide Prepared according to the procedure of Example 25 using 3-amino-4-methoxy-N-phenyl-benzamide (0.8 g, 3.2 mmol), tris(2-methoxyphenyl)bismuthine (1.8 g, 3.4 mmol), copper(II) acetate (0.6 g, 3.4 mmol), and triethylamine (0.34 g, 3.4 mmol) to afford the product (0.9 g); m.p. 155-156 C. after chromatography on a column of silica gel in chloroform followed by recrystallization from ethanol.
  • 4
  • [ 120-35-4 ]
  • [ 33756-91-1 ]
  • 3-(3-chlorophenylamino)-4-methoxy-N-phenylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine;copper diacetate; In chloroform; ethyl acetate; Example 31 3-(3-Chloro-phenylamino)-4-methoxy-N-phenyl-benzamide Prepared according to the procedure of Example 25 using 3-amino-4-methoxy-N-phenyl-benzamide (1.5 g, 6.2 mmol), tris(3-chlorophenyl)bismuthine (3.5 g, 6.4 mmol), copper(II) acetate (1.16 g, 6.4 mmol), and triethylamine (0.65 g, 6.4 mmol) to give a solid which was purified by chromatography on a column of silica gel in chloroform/ethyl acetate 99:1 to afford the product (1.8 g); m.p. 168-170 C. after recrystallization from ethanol. Calculated for C20H17ClN2O2: C, 68.09; H, 4.86; N, 7.94. Found: C, 67.91; H, 4.71; N, 7.80.
  • 5
  • [ 120-35-4 ]
  • tris(3,5-dimethylphenyl)-bismuthine [ No CAS ]
  • 3-(3,5-dimethyl-phenylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine;copper diacetate; Example 36 3-(3,5-Dimethyl-phenylamino)-4-methoxy-N-phenyl-benzamide Prepared according to the procedure of Example 25 using 3-amino-4-methoxy-N-phenyl-benzamide (1.5 g, 6.3 mmol), tris(3,5-dimethylphenyl)-bismuthine (3.3 g, 6.3 mmol), copper(II) acetate (1.15 g, 6.3 mmol), and triethylamine (0.64 g, 6.3 mmol) to afford the product (1.1 g); m.p. 198-199 C. after recrystallization from a mixture of dichloromethane and ethyl acetate 10:1. Calculated for C22H22N2O2.0.5CH2Cl2: C, 75.52; H, 6.35; N, 7.99. Found: C, 75.56; H, 6.32; N, 7.92.
  • 6
  • [ 120-35-4 ]
  • C14H12N3O2(1+)*Na(1+) [ No CAS ]
  • 7
  • [ 120-35-4 ]
  • [ 55805-64-6 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium nitrite; In water; at 0℃; for 1h; (EXAMPLE 7); (Preparation of Solution A); In 75 g of ultra pure water is dispersed 5 g (0.021 mol) of <strong>[120-35-4]3-amino-4-methoxybenzanilide</strong>, and the resultant dispersion is cooled to 0C with stirring in an ice bath to which methanol has been added. Further, 6 g (0.058 mol) of 35% hydrochloric acid is added, and the resultant mixture is stirred for 10 minutes. Thereafter, 1.45 g (0.021 mol) of sodium nitrite is dissolved in 2 ml of ultra pure water, and the solution is then added to the mixture. After stirring the mixture for 60 minutes, 0.2 g (0.002 mol) of sulfamic acid is added to eliminate nitrous acid, thereby preparing a diazonium salt solution.
With hydrogenchloride; sodium nitrite; at 5℃;Industry scale;Product distribution / selectivity; 3-Amino-4-methoxybenzanilide was diazotized in a manner known per se in the art by using a 3.5-fold molar amount of hydrochloric acid and an equimolar amount of sodium nitrite, followed by the addition of sodium acetate to prepare a 0.025 mole/L diazo solution of pH 4.0 (40 L, solution temperature: 5 C.). On the side, N-(4-chloro-2,5-dimethoxyphenyl)-3-hydroxy-2-napthaleneca rboxamide (naphthol AS-LC) (362 parts) was dissolved in an aqueous solution, which contained sodium hydroxide (100 parts), to prepare a 0.126 mole/L grounding solution (8 L, solution temperature: 20 C.); 3-Amino-4-methoxybenzanilide was diazotized in a manner known per se in the art by using a 3.5-fold molar amount of hydrochloric acid and an equimolar amount of sodium nitrite, followed by the addition of sodium acetate to prepare a 0.05 mole/L diazo solution of pH 4.0 (20 L, solution temperature: 5 C.). As a grounding solution, on the other hand, the grounding solution (8L, solution temperature: 20 C.) prepared in Example 3 was used. As illustrated in FIG. 3, the diazo solution was next caused to flow as a first fluid I at a flow rate of 5 L/min by the feed pump d from the first feed tank 2 into the ejector 1 through the first flow path a. Owing to depressurization occurred in the ejector 1, the grounding solution was drawn as a second fluid II at a flow rate of 1 L/min (adjusted by the first flow control means e) from the second feed tank 3 through the second flow path b into the ejector 1 maintained at 20 C. by the temperature control means g, and through a coupling reaction, a naphthol AS pigment (PR146) was yielded.
Open the exhaust butterfly valve,2000KG water was injected into the diazo reaction tank,29.3 parts of hydrochloric acid was added and the agitator was started.14.6 parts of red-based KD were added from the manhole,Stirred for 10 minutes,Cooled to 0 C or lower with ice,A solution of 4.6 parts of sodium nitrite, which was completely dissolved, was quickly added,A minute later with potassium iodide test paper was purple.Maintaining the temperature of the diazo component below 5 C,After 1.5 hours, 0.5 parts of sulfamic acid (preliminarily dissolved) was added,Two minutes after potassium iodide test strip diazonium salt solution is colorless,Turn off the blender butterfly valve.
YieldReaction ConditionsOperation in experiment
Exemplary amines and diamines useful in the invention are: ... 2-methoxy-5-nitro-aniline 5-aminoisophthalic acid dimethyl ester 2-aminobenzoic acid 2-trifluoromethylaniline 3-amino-4-methoxybenzanilide
2,4- and 2,5-dichloraniline, ... 2-methoxy-5-methyl-4-aminobenzene sulphonic acid methyl amide, 2,5-dimethoxy-4-aminobenzoic sulphonic acid anilide, 2-methoxy-5-methyl-4-benzoylaminoaniline, 4-ethoxy-3-aminobenzamide, 4-methoxy-3-aminobenzoic acid anilide, 4-methyl-3-aminobenzoic acid -2'4'-dimethylanilide, 4-methyl-3-aminobenzoic acid-4'-chloranilide, 4-chloro-3-aminobenzoic acid-2'4'5'-trichloranilide, ...
A process according to claim 1 wherein the diazotizable amine is selected from the group consisting of 2,4- and 2,5-dichloraniline, ... 2-methoxy-5-methyl-4-aminobenzene sulphonic acid methyl amide, 2,5-dimethoxy-4-aminobenzoic sulphonic acid anilide, 2-methoxy-5-methyl-4-benzoylaminoaniline, 4-ethoxy-3-aminobenzamide, 4-methoxy-3-aminobenzoic acid anilide, 4-methyl-3-aminobenzoic acid-2'4'-dimethylanilide, 4-methyl-3-aminobenzoic acid-4'-chloranilide, 4-chloro-3-aminobenzoic acid-2'-methyl-5'-chloranilide, ...
Representative compounds of formula (1) that may be employed are: ... N'-n-butyl-3-amino-4-methoxybenzenesulfonamide N'-(gamma-methoxypropyl)-3-amino-4-methoxybenzenesulfonamide N'-methyl-3-amino-4-methoxybenzenesulfonamide 3-amino-4-methoxyphenylbenzylsulfone 3-amino-4-methoxybenzanilide 2-amino-1-phenol-4-sulfonanilide 2-amino-4-(methylsulfonyl)phenol 4-amino-3-hydroxy-4'-chlorobenzenesulfonanilide ...
Exemplary amines and diamines useful in the invention are: ... 2-aminobenzoic acid 2-trifluoromethylaniline 3-amino-4-methoxybenzanilide

  • 9
  • [ 120-35-4 ]
  • [ 169762-05-4 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; trichlorophosphate; In water; N,N-dimethyl-aniline; Step A Preparation of 3-Amino-4-methoxy-4'-N,N-Di-methylaminobenzophenone STR262 Fifty grams (0.2 mole) of <strong>[120-35-4]3-amino-4-methoxybenzanilide</strong>, 70 g (0.58 mole) N,N-dimethylaniline and 36 g POCl3 were heated on a water bath at 90 C. to 95 C. for 4 to 6 hours. The product was then cautiously poured into a solution of 23 ml of concentrated hydrochloric acid in 250 ml water. The resulting solution was warmed at 80 C. until the initial reddish color disappeared, indicating that the aniline was completely hydrolyzed. A liter of water was added to precipitate the ketone, which was filtered, washed with cold water, and recrystallized from a 2:1 aqueous alcohol solution. Yield: 38 g of slightly yellowish crystals, metling point 82 C.
  • 10
  • [ 98-88-4 ]
  • [ 97-00-7 ]
  • [ 120-35-4 ]
YieldReaction ConditionsOperation in experiment
79% EXAMPLE 5 3-Amino-4-Methoxybenzanilide According to the procedure of Example 1, substituting 135.5 g. of benzoyl chloride for the acetic anhydride used therein, 2,4-dinitrochlorobenzene was converted to 3-amino-4-methoxybenzanilide, in 79% yield.
  • 11
  • [ 120-35-4 ]
  • [ 23163-86-2 ]
  • 3-[3-(4-Chloro-3-trifluoromethylphenyl)-thioureido]-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethyl acetate; Example 73 3-[3-(4-Chloro-3-trifluoromethylphenyl)-thioureido]-4-methoxy-N-phenyl-benzamide Prepared according to the procedure described for Example 60 using 3-amino-4-methoxy-N-phenyl-benzamide (0.972 g, 4.0 mmol) and 4-chloro-3-(trifluoromethyl)phenyl isothiocyanate (0.961 g, 4.0 mmol). Trituration in hexanes/ethyl acetate (3:2) gave the product (1.91 g); m.p. 172-173 C. Calculated for C23H17Cl2N3O2S: C, 55.06; H, 3.57; N, 8.76. Found: C, 54.88; H, 3.26; N, 8.58.
  • 12
  • [ 120-35-4 ]
  • [ 66-77-3 ]
  • 4-Methoxy-3-[(naphthalen-1-ylmethyl)-amino]-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 217 4- Methoxy-3-[(naphthalen-1-ylmethyl)-amino]-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 1-naphthaldehyde as starting materials, which are commercially available from Aldrich; m.p. 172-174 C.
  • 13
  • [ 120-35-4 ]
  • [ 105-07-7 ]
  • 3-(4-Cyano-benzylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 233 3-(4-Cyano-benzylamino)-4-methoxy-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 4-cyanobenzaldehyde as starting materials, which are commercially available from Aldrich; m.p. 130-133 C.
  • 14
  • [ 120-35-4 ]
  • [ 1571-08-0 ]
  • 4-[(2-Methoxy-5-phenylcarbamoyl-phenylamino)-methyl]-benzoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 221 4-[(2-Methoxy-5-phenylcarbamoyl-phenylamino)-methyl]-benzoic acid methyl ester The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide or 4-carbomethoxybenzaldehyde as starting materials, which are commercially available from Aldrich; m.p. 170-172 C.
  • 15
  • [ 120-35-4 ]
  • [ 135-02-4 ]
  • 4-Methoxy-3-(2-methoxy-benzylamino)-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 238 4-Methoxy-3-(2-methoxy-benzylamino)-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 2-methoxybenzaldehyde as starting materials, which are commercially available from Aldrich; m.p. 177-179 C.
  • 16
  • [ 120-35-4 ]
  • [ 456-48-4 ]
  • 4-Methoxy-3-(3-fluoro-benzylamino)-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 214 4-Methoxy-3-(3-fluoro-benzylamino)-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 3-fluorobenzaldehyde as starting materials, which are commercially available from Aldrich; m.p. 137-140 C.
  • 17
  • [ 34036-07-2 ]
  • [ 120-35-4 ]
  • 3-(3,4-Difluoro-benzylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 274 3-(3,4-Difluoro-benzylamino)-4-methoxy-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 3,4-difluorobenzaldehyde as starting materials, which can be purchased from Aldrich; m.p. 150-152 C.
  • 18
  • [ 120-35-4 ]
  • [ 104-87-0 ]
  • 4-Methoxy-3-(4-methyl-benzylamino)-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 237 4-Methoxy-3-(4-methyl-benzylamino)-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 4-methylbenzaldehyde as starting materials, which are commercially available from Aldrich; m.p. 184-186 C.
  • 19
  • [ 120-35-4 ]
  • [ 446-52-6 ]
  • 4-Methoxy-3-(2-fluoro-benzylamino)-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 270 4-Methoxy-3-(2-fluoro-benzylamino)-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 2-fluorobenzaldehyde as starting materials, which can be purchased from Aldrich; m.p 142-144 C.
  • 20
  • [ 120-35-4 ]
  • [ 620-23-5 ]
  • 4-Methoxy-3-(3-methyl-benzylamino)-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 273 4-Methoxy-3-(3-methyl-benzylamino)-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 3-methylbenzaldehyde as starting materials, which can be purchased from Aldrich; m.p. 184-185 C.
  • 21
  • [ 454-89-7 ]
  • [ 120-35-4 ]
  • 4-Methoxy-3-(3-trifluoromethyl-benzylamino)-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 269 4-Methoxy-3-(3-trifluoromethyl-benzylamino)-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 3-trifluoromethylbenzaldehyde as starting materials, which can be purchased from Aldrich; m.p. 167-171 C.
  • 22
  • [ 120-35-4 ]
  • [ 3218-36-8 ]
  • 3-[(Biphenyl-4-ylmethyl)-amino]-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 236 3-[(Biphenyl-4-ylmethyl)-amino]-4-methoxy-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 4-phenylbenzaldehyde as starting materials, which are commercially available from Aldrich; m.p. 222-223 C.
  • 23
  • [ 120-35-4 ]
  • [ 587-04-2 ]
  • 3-(3-Chloro-benzylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 231 3-(3-Chloro-benzylamino)-4-methoxy-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 3-chlorobenzaldehyde as starting materials, which are commercially available from Aldrich; m.p. 203-205 C.
  • 24
  • [ 24964-64-5 ]
  • [ 120-35-4 ]
  • 3-(3-Cyano-benzylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 229 3-(3-Cyano-benzylamino)-4-methoxy-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 3-cyanobenzaldehyde as starting materials, which are commercially available from Aldrich; m.p. 172-174 C.
  • 25
  • [ 120-35-4 ]
  • [ 99-61-6 ]
  • 4-Methoxy-3-(3-nitro-benzylamino)-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 215 4-Methoxy-3-(3-nitro-benzylamino)-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 3-nitrobenzaldehyde as starting materials, which are commercially available from Aldrich; m.p. 172-175 C.
  • 26
  • [ 98-03-3 ]
  • [ 120-35-4 ]
  • 4-Methoxy-3-[(thiophen-2-ylmethyl)-amino]-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 259 4-Methoxy-3-[(thiophen-2-ylmethyl)-amino]-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 2-thiophenecarboxaldehyde as starting materials, which are commercially available from Aldrich; m.p. 195-197 C.
  • 27
  • [ 120-35-4 ]
  • [ 120-14-9 ]
  • 3-(3,4-Dimethoxy-benzylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride; acetic acid; Example 52 3-(3,4-Dimethoxy-benzylamino)-4-methoxy-N-phenyl-benzamide Prepared according to the procedure of Example 50 using 3,4-dimethoxybenzaldehyde (1.94 g, 11.6 mmol), 3-amino-4-methoxy-N-phenyl-benzamide (2.8 g, 11.6 mmol), acetic acid (0.69 g, 11.5 mmol), and sodium triacetoxyborohydride (2.6 g, 11.7 mmol) to afford the product (2.9 g); m.p. 187-188 C. after recrystallization from ethanol. Calculated for C23H24N2O4: C, 70.39; H, 6.16; N, 7.14. Found: C, 70.31; H, 6.00; N, 7.10.
  • 28
  • [ 120-35-4 ]
  • [ 100-10-7 ]
  • 3-(4-Dimethylamino-benzylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 268 3-(4-Dimethylamino-benzylamino)-4-methoxy-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 4-dimethylaminobenzaldehyde as starting materials, which can be purchased from Aldrich; m.p. 195-197 C.
  • 29
  • [ 3032-81-3 ]
  • [ 120-35-4 ]
  • 3-(3,5-Dichloro-phenylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;copper(I) iodide; In dichloromethane; Example 35 3-(3,5-Dichloro-phenylamino)-4-methoxy-N-phenyl-benzamide Prepared according to the procedure of Example 33 using 3-amino-4-methoxy-N-phenyl-benzamide (2.0 g, 8.3 mmol), 3,5-dichloroiodobenzene (4.5 g, 16.5 mmol), potassium carbonate (2.9 g, 21.0 mmol), and copper(I) iodide (0.5 g, 2.6 mmol) to give a gummy residue which was subjected to chromatography on a column of silica gel in dichloromethane to afford the product (0.3 g); m.p. 207-208° C. after recrystallization from ethanol. Calculated for C20H16Cl2N2O2.0.2C2H6O: C, 61.80; H, 4.37; N, 7.07. Found: C, 61.47; H, 4.04; N, 7.08.
  • 30
  • [ 2131-62-6 ]
  • [ 120-35-4 ]
  • 4-[3-(2-Methoxy-5-phenylcarbamoyl-phenyl)-thioureido]-benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 75 4-[3-(2-Methoxy-5-phenylcarbamoyl-phenyl)-thioureido]-benzoic acid Prepared according to the procedure described for Example 60 using 3-amino-4-methoxy-N-phenyl-benzamide (0.972 g, 4.0 mmol) and 4-carboxyphenyl isothiocyanate (0.722 g, 4.0 mmol) to afford the product (1.369 g); m.p. 201-202 C. Calculated for C22H19N3O4S.0.25 H2O: C, 62.03; H, 4.61; N, 9.87. Found: C, 61.92; H, 4.73; N, 9.59.
  • 31
  • [ 120-35-4 ]
  • [ 1939-99-7 ]
  • 3-Phenylmethanesulfonylamino-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; Example 135 3-Phenylmethanesulfonylamino-4-methoxy-N-phenyl-benzamide Prepared according to the procedure described for Example 121 using benzylsulfonyl chloride (1.90 g, 10 mmol), 3-amino-4-methoxy-N-phenyl-benzamide (2.43 g, 10 mmol), and pyridine (25 mL) to afford the product (2.5 g); m.p. 216-216 C. after trituration in hexanes/ethyl acetate (1:1).
  • 32
  • [ 56542-67-7 ]
  • [ 120-35-4 ]
  • 3-(3-Cyano-benzenesulfonylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 195 3-(3-Cyano-benzenesulfonylamino)-4-methoxy-N-phenyl-benzamide The title compound has been made using the procedure of Example 121, but using 3-amino-4-methoxy-N-phenyl benzamide and 3-cyanobenzenesulfonyl chloride as starting materials, which is commercially available from Aldrich or Maybridge; m.p. 195-197 C.
  • 33
  • [ 120-35-4 ]
  • [ 614-69-7 ]
  • 4-Methoxy-N-phenyl-3-(3-o-tolyl-thioureido)-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethyl acetate; Example 98 4-Methoxy-N-phenyl-3-(3-o-tolyl-thioureido)-benzamide A mixture of 3-amino-4-methoxy-N-phenyl-benzamide (0.972 g, 4.00 mmol), 2-methylphenyl isothiocyanate (0.55 mL, 4.11 mmol, and ethyl acetate 20 mL) was allowed to stand at room temperature. After 4 days, the reaction was heated to 80 C. for 3 hours then allowed to stand at room temperature for an additional 5 days. Filtration afforded the product (0.804 g); m.p. 172-174 C. Calculated for C22H21N3O2S: C, 67.50; H, 5.41; N, 10.73. Found: C, 66.96; H, 5.47; N, 10.56.
  • 34
  • [ 98-01-1 ]
  • [ 120-35-4 ]
  • 3-[(Furan-3-ylmethyl)-amino]-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 222 3-[(Furan-3-ylmethyl)-amino]-4-methoxy-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 2-furaldehyde as starting materials, which are commercially available from Aldrich; m.p. 188-190 C.
  • 35
  • [ 1645-65-4 ]
  • [ 120-35-4 ]
  • 4-Methoxy-N-phenyl-3-[3-(4-trifluoromethyl-phenyl)-thioureido]-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 63 4-Methoxy-N-phenyl-3-[3-(4-trifluoromethyl-phenyl)-thioureido]-benzamide Prepared according to the procedure described for Example 60 using 3-amino-4-methoxy-N-phenyl-benzamide (0.198 g, 0.82 mmol) and 4-(trifluoromethyl)phenyl isothiocyanate (0.169 g, 0.83 mmol) to give the product (0.306 g); m.p. 194-196 C. Calculated for C22H18F3N3O2S: C, 59.32; H, 4.07; N, 9.43. Found: C, 59.04; H, 4.05; N, 9.35.
  • 36
  • [ 120-35-4 ]
  • [ 120-21-8 ]
  • 3-(4-Diethylamino-benzylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 211 3-(4-Diethylamino-benzylamino)-4-methoxy-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 4-diethylaminobenzaldehyde as starting materials, which are commercially available from Aldrich; m.p. 180-181 C.
  • 37
  • [ 619-21-6 ]
  • [ 120-35-4 ]
  • 3-[(2-Methoxy-5-phenylcarbamoyl-phenylamino)-methyl]-benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 241 3-[(2-Methoxy-5-phenylcarbamoyl-phenylamino)-methyl]-benzoic acid The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 3-carboxybenzaldehyde as starting materials, which are commercially available from Aldrich; m.p. 210-212 C.
  • 38
  • [ 704-13-2 ]
  • [ 120-35-4 ]
  • 3-(3-Hydroxy-4-nitro-benzylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 228 3-(3-Hydroxy-4-nitro-benzylamino)-4-methoxy-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 3-hydroxy-4-nitrobenzaldehyde as starting materials which are commercially available from Aldrich; m.p. 140-143 C.
  • 39
  • [ 120-35-4 ]
  • [ 619-66-9 ]
  • 4-[(2-Methoxy-5-phenylcarbamoyl-phenylamino)-methyl]-benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 278 4-[(2-Methoxy-5-phenylcarbamoyl-phenylamino)-methyl]-benzoic acid The title compound has been made using the procedure of Example 50, but using <strong>[120-35-4]3-amino-4-methoxy-benzanilide</strong> and 4carboxybenzaldehyde, which are available from Aldrich, as starting materials; mp >240 C.
  • 40
  • [ 120-35-4 ]
  • [ 594-44-5 ]
  • 3-Ethanesulfonylamino-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; Example 134 3-Ethanesulfonylamino-4-methoxy-N-phenyl-benzamide Prepared according to the procedure described for Example 121 using ethanesulfonyl chloride (1.5 mL, 15.8 mmol), 3-amino-4-methoxy-N-phenyl-benzamide (2.43 g. 10 mmol) and pyridine (25 mL) to afford the product (3.023 g); m.p. 175-177 C. after trituration in hexanes/ethyl acetate (1:1).
  • 41
  • [ 10130-89-9 ]
  • [ 120-35-4 ]
  • 4-(2-Methoxy-5-phenylcarbamoyl-phenylsulfamoyl)-benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 183 4-(2-Methoxy-5-phenylcarbamoyl-phenylsulfamoyl)-benzoic acid The title compound has been made using the procedure of Example 121, but using 3-amino-4-methoxy-N-phenyl benzamide and 4-carboxybenzenesulfonyl chloride as starting materials, which are commercially available from Aldrich; m.p. 212-214 C.
  • 42
  • [ 878-00-2 ]
  • [ 120-35-4 ]
  • acetic acid 4-[(2-methoxy-5-phenylcarbamoyl-phenylamino)-methyl]-phenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 220 Acetic acid 4-[(2-methoxy-5-phenylcarbamoyl-phenylamino)-methyl]-phenyl ester The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 4-acetoxybenzaldehyde as starting materials, which are commercially available from Aldrich; m.p. 193-195 C.
  • 43
  • [ 120-35-4 ]
  • [ 144-55-8 ]
  • 3-Benzylamino-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride; benzaldehyde; acetic acid; In dichloromethane; Example 50 3-Benzylamino-4-methoxy-N-phenyl-benzamide Benzaldehyde (2.2 g, 21.0 mmol) was added to a stirred solution of 3-amino-4-methoxy-N-phenyl-benzamide (5.0 g, 21.0 mmol) in dichloromethane (250 mL) under an inert atmosphere at room temperature, followed by acetic acid (1.26 g, 21.0 mmol). After 1 hour sodium triacetoxyborohydride (4.7 g, 21.0 mmol) was added in one portion. After 18 hours, saturated aqueous sodium bicarbonate (200 mL) was added and the mixture stirred for 2 to 3 hours. The layers were separated, the organic phase was washed with water then saturated aqueous sodium chloride, then dried over MgSO4. The solution was filtered and stripped of solvent under reduced pressure to afford the product (6.5 g); m.p. 164-165 C. after recrystallization from ethanol. Calculated for C21H20N2O2: C, 75.88; H, 6.06; N, 8.43. Found: C, 75.62; H, 6.02; N, 8.44.
  • 44
  • [ 17452-27-6 ]
  • [ 120-35-4 ]
  • 4-Methoxy-N-phenyl-3-(3-pyridin-3-yl-thioureido)-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethyl acetate; Example 81 4-Methoxy-N-phenyl-3-(3-pyridin-3-yl-thioureido)-benzamide Prepared according to the procedure described for Example 60 using 3-amino-4-methoxy-N-phenyl-benzamide (0.972 g, 4.00 mmol) and 3-pyridyl isothiocyanate (0.565 g, 4.15 mmol). Trituration in hexanes/ethyl acetate (3:2) gave the product (1.441 g); m.p. 178-179 C. Calculated for C20H18N4O2S: C, 63.47; H, 4.79; N, 14.80. Found: C, 62.88; H, 4.78; N, 14.65.
  • 45
  • [ 120-35-4 ]
  • [ 2131-61-5 ]
  • 4-Methoxy-3-[3-(4-nitrophenyl)-thioureido]-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 88 4-Methoxy-3-[3-(4-nitrophenyl)-thioureido]-N-phenyl-benzamide Prepared according to the procedure described for Example 60 using 3-amino-4-methoxy-N-phenyl-benzamide (0.976 g, 4.02 mmol) and 4-nitrophenyl isothiocyanate (0.723 g, 4.02 mmol) to afford the product (1.39 g) after trituration in ether; m.p. 183-184 C.
  • 46
  • [ 120-35-4 ]
  • [ 2284-20-0 ]
  • 4-Methoxy-3-[3-(4-methoxy-phenyl)-thioureido]-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methane; dichloromethane; Example 83 4-Methoxy-3-[3-(4-methoxy-phenyl)-thioureido]-N-phenyl-benzamide Prepared according to the procedure described for Example 60 using 3-amino-4-methoxy-N-phenyl-benzamide (0.972 g, 4.00 mmol) and 4-methoxyphenyl isothiocyanate (0.77 g, 5.16 mmol), except that after collection of the product obtained upon trituration with hexanes/ethyl acetate, an impurity was present. The impurity was removed by slurrying the solid in dichloromethane/methane 95:5 followed by filtration to afford the product (0.505 g); m.p. 168-169 C. Calculated for C22H21N3O3S: C, 64.85; H, 5.19; N, 10.31. Found: C, 64.55; H, 5.17; N, 10.18.
  • 47
  • [ 120-35-4 ]
  • [ 98-74-8 ]
  • 4-Methoxy-(4-nitro-benzenesulfonylamino)-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 188 4-Methoxy-(4-nitro-benzenesulfonylamino)-N-phenyl-benzamide The title compound has been made using the procedure of Example 121, but using 3-amino-4-methoxy-N-phenyl benzamide and 4-nitrobenzenesulfonyl chloride as starting materials, which are commercially available from Aldrich; m.p. 224-227 C.
  • 48
  • [ 120-35-4 ]
  • [ 622-59-3 ]
  • 4-Methoxy-N-phenyl-3-(-3-p-tolyl-thioureido)-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethyl acetate; Example 69 4-Methoxy-N-phenyl-3-(-3-p-tolyl-thioureido)-benzamide Prepared according to the procedure described for Example 60 using 3-amino-4-methoxy-N-phenyl-benzamide (0.243 g, 1.0 mmol) and 4-methylphenyl isothiocyanate (0.205 g, 1.38 mmol). The reaction was incomplete after 2 days, so the mixture was diluted to 30 mL with ethyl acetate, and a small additional portion of 4-methylphenyl isothiocyanate was added. The mixture was boiled on a steambath until no solvent remained and the residue triturated in hexanes/ethyl acetate (4:1) and filtered to afford the product (0.255 g); m.p. 156-158 C. CI Mass Spectrum: [M+H+]+=392. Calculated for C22H21N3O2S.0.5 H2O: C, 65.97; H, 5.54; N, 10.49. Found: C, 66.16; H, 5.60; N, 10.31.
  • 49
  • [ 120-35-4 ]
  • [ 2131-64-8 ]
  • 3-[3-(4-Dimethylaminophenyl)-thioureido]-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethyl acetate; Example 93 3- [3-(4-Dimethylaminophenyl)-thioureido]-4-methoxy-N-phenyl-benzamide A mixture of 3-amino-4-methoxy-N-phenyl-benzamide (0.975 g, 4.01 mmol), 4-(dimethylamino)phenyl isothiocyanate (0.716 g, 4.00 mmol), and ethyl acetate (20 mL) was allowed to stand at room temperature. After 5 days, the mixture was concentrated to two-thirds volume by rotary evaporator, allowed to stand overnight, then heated to 80 degrees for 4 hours. The precipitate was collected by filtration and the mother liquor heated to 80 degrees for another 3 hours. More precipitate was collected by filtration and the mother liquor again heated to 80 degrees and after 7 hours allowed to cool to room temperature overnight. The remaining liquor was concentrated to dryness and the residue triturated in hexanes and the solid filtered off and washed with ethyl acetate. Combination of all the lots gave the product (0.905 g); m.p. 179-180 C. Calculated for C23H24N4O2S.0.1 M EtOAc: C, 65.46; H, 5.82; N, 13.05. Found: C, 65.24; H, 5.70; N, 12.86.
  • 50
  • [ 16629-19-9 ]
  • [ 120-35-4 ]
  • 3-(Thiophene-2-sulfonylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; Example 142 3-(Thiophene-2-sulfonylamino)-4-methoxy-N-phenyl-benzamide Prepared according to the procedure described for Example 121 using 2-thiophenesulfonyl chloride (1.82 g, 10 mmol), 3-amino-4-methoxy-N-phenyl-benzamide (2.43 g, 10 mmol), and pyridine (25 mL) to afford the product (3.457 g); m.p. 180-183 C. after trituration in hexanes/ethyl acetate (1:1).
  • 51
  • [ 120-35-4 ]
  • [ 123-08-0 ]
  • 3-(4-Hydroxy-benzylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 272 3-(4-Hydroxy-benzylamino)-4-methoxy-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 4-hydroxybenzaldehyde as starting materials, which can be purchased from Aldrich; m.p. 188-190 C.
  • 52
  • [ 120-57-0 ]
  • [ 120-35-4 ]
  • 3-[(Benzo[1,3]dioxol-5-ylmethyl)-amino]-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 266 3-[(Benzo[1,3]dioxol-5-ylmethyl)-amino]-4-methoxy-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 3,4-methylenedioxybenzaldehyde as starting materials, which can be purchased from Aldrich; m.p. 185-187 C.
  • 53
  • [ 120-35-4 ]
  • [ 2131-55-7 ]
  • 3-[3-(4-Chlorophenyl)-thioureido]-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethyl acetate; Example 65 3-[3-(4-Chlorophenyl)-thioureido]-4-methoxy-N-phenyl-benzamide Prepared according to the procedure described for Example 60 using 3-amino-4-methoxy-N-phenyl-benzamide (0.243 g, 1.0 mmol) and 4-chlorophenyl isothiocyanate (0.174 g, 1.03 mmol). Trituration in hexanes/ethyl acetate (1:1) gave the product (0.362 g); m.p. 179-180 C. Calculated for C21H18ClN3O2S: C, 61.23; H, 4.40; N, 10.20. Found: C, 60.94; H, 4.23; N, 10.03.
  • 54
  • [ 120-35-4 ]
  • [ 103-72-0 ]
  • 4-Methoxy-N-phenyl-3-(3-phenyl-thioureido)-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 62 4-Methoxy-N-phenyl-3-(3-phenyl-thioureido)-benzamide Prepared according to the procedure described for Example 60 using 3-amino-4-methoxy-N-phenyl-benzamide (0.245 g, 1.01 mmol) and phenyl isothiocyanate (0.12 mL, 1.00 mmol) to give the product (0.216 g); m.p. 174-176 C. Calculated for C21H19N3O2S: C, 66.82; H, 5.07; N, 11.13. Found: C, 66.34; H, 5.13; N, 11.04.
  • 55
  • [ 120-35-4 ]
  • [ 98-59-9 ]
  • 3-(4-Methyl-benzenesulfonylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 124 3-(4-Methyl-benzenesulfonylamino)-4-methoxy-N-phenyl-benzamide Prepared according to the procedure described for Example 121 using 4-methylbenzenesulfonyl chloride (2.06 g, 10 mmol) and 3-amino-4-methoxy-N-phenyl-benzamide (2.43 g, 10.0 mmol) to afford the product (3.053 g); m.p. 200-202 C. Calculated for C21H20N2O4S: C, 63.62; H, 5.08; N, 7.07. Found: C, 63.43; H, 5.18; N, 6.86.
  • 56
  • [ 2386-60-9 ]
  • [ 120-35-4 ]
  • 3-(Butane-1-sulfonylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 129 3-(Butane-1-sulfonylamino)-4-methoxy-N-phenyl-benzamide Prepared according to the procedure described for Example 128 using 1-butanesulfonyl chloride (0.47 g, 3.0 mmol) and 3-amino-4-methoxy-N-phenyl-benzamide (0.73 g, 3.0 mmol) to afford the product (1.0 g); m.p. 182-183 C. after recrystallization from ethanol. Calculated for C18H22N2O4S: C, 59.65; H, 6.12; N, 7.73. Found: C, 59.68; H, 6.09; N, 7.60.
  • 57
  • [ 939-97-9 ]
  • [ 120-35-4 ]
  • 3-(4-tert-Butyl-benzylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 232 3-(4-tert-Butyl-benzylamino)-4-methoxy-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 4-tert-butylbenzaldehyde as starting materials, which are commercially available from Aldrich; m.p. 195-197 C.
  • 58
  • [ 120-35-4 ]
  • [ 137049-00-4 ]
  • 3-(1-Methyl-1H-imidazole-4-sulfonylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; Example 141 3-(1-Methyl-1H-imidazole-4-sulfonylamino)-4-methoxy-N-phenyl-benzamide Pyridine (25 mL) was added to a mixture of 3-amino-4-methoxy-N-phenyl-benzamide (2.43 g, 10 mmol) and 1-methylimidazole-4-sulfonyl chloride (1.82 g, 10 mmol) and the mixture agitated then allowed to stand at room temperature. After 4 days, the mixture was partitioned between ethyl acetate (400 mL) and water (400 mL). The insoluble material was collected by filtration, washed with water, and air dried. The organic extract was washed with water (2*400 mL), 1N HCl (100 mL), and brine (100 mL), then dried over magnesium sulfate, filtered, and stripped of solvent. The residue was combined with the solid obtained above to afford the product (3.07 g); m.p. 250-252 C., after trituration in hexanes/ethyl acetate (1:1).
  • 59
  • [ 69812-29-9 ]
  • [ 120-35-4 ]
  • 3-(2-Acetylamino-4-methyl-thiazole-5-sulfonylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 131 3-(2-Acetylamino-4-methylthiazole-5sulfonylamino)-4-methoxy-N-phenyl-benzamide Prepared according to the procedure described for Example 126 using 2-acetamido-4-methyl-5-thiazolesulfonyl chloride (0.76 g, 3.0 mmol) and 3-amino-4-methoxy-N-phenyl-benzamide (0.73 g, 3.0 mmol) to afford the product (0.7 g); m.p. 260-261 C. after trituration in diethyl ether. Calculated for C20H20N4O5S2: C, 52.16; H, 4.38; N, 12.17. Found: C, 52.15; H, 4.26; N, 11.87.
  • 60
  • [ 81606-31-7 ]
  • [ 120-35-4 ]
  • 3-(4,5-Dibromo-thiophene-2-sulfonylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; Example 126 3-(4,5-Dibromothiophene-2-sulfonylamino)-4-methoxy-N-phenyl-benzamide Pyridine (5 mL) was added to a mixture of 3-amino-4-methoxy-N-phenyl-benzamide (0.73 g, 3.0 mmol) and 2,3-dibromothiophene-5-sulfonyl chloride (1.0 g, 3.0 mmol) and stirred under an inert atmosphere at room temperature. After 20 hours, the mixture was diluted with water (50 mL), acidified with 4N HCl, and extracted with dichloromethane (2*50 mL). The insoluble material was filtered off and rinsed with water. The combined extracts were washed successively with 2N HCl, water, and saturated brine, then dried over MgSO4. The solvent was removed under reduced pressure and the residue combined with the solid from above to afford the product (0.7 g), m.p. 205-210 C., after recrystallization from ethanol. Calculated for C18H14Br2N2O4S2.0.3 EtOH: C, 39.89; H, 2.58; N, 5.00. Found: C, 40.26; H, 2.65; N, 5.18.
  • 61
  • [ 18704-37-5 ]
  • [ 120-35-4 ]
  • 3-(Quinoline-8-sulfonylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 130 3-(Quinoline-8-sulfonylamino)-4-methoxy-N-phenyl-benzamide Prepared according to the procedure described for Example 126 using 8-quinolinesulfonyl chloride (0.68 g, 3.0 mmol) and 3-amino-4-methoxy-N-phenyl-benzamide (0.73 g, 3.0 mmol) to afford the product (1.0 g); m.p. 187-188 C. after trituration in diethyl ether and recrystallization from ethanol. Calculated for C23H19N3O4S: C, 63.73; H, 4.42; N, 9.69. Found: C, 63.68; H, 4.40; N, 9.66.
  • 62
  • [ 120-35-4 ]
  • [ 121-51-7 ]
  • 3-(3-Nitro-benzenesulfonylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 122 3-(3-Nitro-benzenesulfonylamino)-4-methoxy-N-phenyl-benzamide Prepared according to the procedure described for Example 121 using 3-nitrobenzenesulfonyl chloride (2.44 g, 10 mmol) and 3-amino-4-methoxy-N-phenyl-benzamide (2.43 g, 10.0 mmol) to afford the product (3.522 g); m.p. 208-210 C. Calculated for C20H17N3O6S: C, 56.20; H, 4.01; N, 9.83. Found: C, 56.43; H, 4.10; N, 9.81.
  • 63
  • [ 5779-95-3 ]
  • [ 120-35-4 ]
  • [ 228424-64-4 ]
YieldReaction ConditionsOperation in experiment
Example 218 4-Methoxy-3-(3,5-dimethyl-benzylamino)-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 3,5-dimethylbenzaldehyde as starting materials, which are commercially available from Aldrich or Lancaster; m.p. 168-170 C.
  • 64
  • [ 7795-95-1 ]
  • [ 120-35-4 ]
  • 4-Methoxy-3-(octane-1-sulfonylamino)-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 178 4-Methoxy-3-(octane-1-sulfonylamino)-N-phenyl-benzamide The title compound has been made using the procedure of Example 127, but using 3-amino-4-methoxy-N-phenyl benzamide and 1-octanesulfonyl chloride as a starting material, which are commercially available from Aldrich and Lancaster; m.p. 154-155 C.
  • 65
  • [ 120-35-4 ]
  • [ 121899-80-7 ]
  • 3-(3-Trifluoromethyl-phenylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine;copper diacetate; Example 30 3-(3-Trifluoromethyl-phenylamino)-4-methoxy-N-phenyl-benzamide Prepared according to the procedure of Example 25 using 3-amino-4-methoxy-N-phenyl-benzamide (0.7 g, 2.9 mmol), tris(3-trifluoromethylphenyl)bismuthine (2.0 g, 3.1 mmol), copper(II) acetate (0.54 g, 3.0 mmol), and triethylamine (0.29 g, 2.9 mmol) to afford the product (0.7 g); m.p. 183-184 C. after recrystallization from acetonitrile. Calculated for C21H17FN2O2: C, 65.28; H, 4.43; N, 7.25. Found: C, 64.89; H, 4.13; N, 7.24.
  • 66
  • [ 120-35-4 ]
  • [ 26919-48-2 ]
  • 3-(3-Methyl-phenylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine;copper diacetate; Example 32 3-(3-Methyl-phenylamino)-4-methoxy-N-phenyl-benzamide Prepared according to the procedure described for Example 25 using 3-amino-4-methoxy-N-phenyl-benzamide (1.0 g, 4.1 mmol), tris(3-methylphenyl)bismuthine (2.2 g, 4.6 mmol), copper(II) acetate (0.8 g, 4.4 mmol), and triethylamine (0.44 g, 4.4 mmol) to afford the product (0.7 g); m.p. 160-161 C. after recrystallization from acetonitrile. Calculated for C21H20N2O2: C, 75.88; H, 6.06; N, 8.43. Found: C, 75.63; H, 6.11; N, 8.47.
  • 67
  • [ 120-35-4 ]
  • [ 5142-75-6 ]
  • 3-(4-Methyl-phenylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine;copper diacetate; Example 34 3-(4-Methyl-phenylamino)-4-methoxy-N-phenyl-benzamide Prepared according to the procedure of Example 25 using 3-amino-4-methoxy-N-phenyl-benzamide (1.1 g, 4.5 mmol), tris(4-methylphenyl)bismuthine (2.5 g, 5.2 mmol), copper(II) acetate (0.82 g, 4.5 mmol), and triethylamine (0.46 g, 4.5 mmol) to afford the product (0.8 g); m.p. 187-188 C. after recrystallization from acetonitrile then ethyl acetate. Calculated for C21H20N2O2: C, 75.88; H, 6.06; N, 8.43. Found: C, 75.57; H, 5.83; N, 8.34.
  • 68
  • [ 19241-24-8 ]
  • [ 120-35-4 ]
  • 3-[3-(4-tert-Butyl-phenyl)-thioureido]-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 64 3-[3-(4-tert-Butyl-phenyl)-thioureido]-4-methoxy-N-phenyl-benzamide Prepared according to the procedure described for Example 60 using 3-amino-4-methoxy-N-phenyl-benzamide (0.216 g, 0.89 mmol) and 4-t-butylphenyl isothiocyanate (0.176 g, 0.92 mmol) to give the product (0.180 g); m.p. 198-200 C. Calculated for C25H27N3O2S.0.33 H2O: C, 68.32; H, 6.34; N, 9.56. Found: C, 68.22; H, 6.49; N, 9.59.
  • 69
  • [ 120-35-4 ]
  • (2,3,5,6-tetrafluorophenyl)isothiocyanate [ No CAS ]
  • 4-Methoxy-N-phenyl-3-[3-(2,3,5,6-tetrafluoro-phenyl)-thioureido]-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 68 4-Methoxy-N-phenyl-3-[3-(2,3,5,6-tetrafluoro-phenyl)-thioureido]-benzamide Prepared according to the procedure described for Example 60 using 3-amino-4-methoxy-N-phenyl-benzamide (0.243 g, 1.0 mmol) and 2,3,5,6-tetrafluorophenyl isothiocyanate (0.224 g, 1.1 mmol) to give the product (0.398 g); m.p. 170-174 C. Calculated for C21H15F4N3O2S: C, 56.12; H, 3.36; N, 9.35. Found: C, 55.74; H, 3.22; N, 9.19.
  • 70
  • [ 3125-71-1 ]
  • [ 120-35-4 ]
  • 3-[3-(3-Acetyl-phenyl)-thioureido]-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 76 3-[3-(3-Acetyl-phenyl)-thioureido]-4-methoxy-N-phenyl-benzamide Prepared according to the procedure described for Example 60 using 3-amino-4-methoxy-N-phenyl-benzamide (0.971 g, 4.00 mmol) and 3-acetylphenyl isothiocyanate (0.709 g, 4.00 mmol) to afford the product (1.135 g); m.p. 176-177 C. Calculated for C23H21N3O3S: C, 65.85; H, 5.05; N, 10.02. Found: C, 65.55; H, 4.93; N, 9.83.
  • 71
  • [ 2131-63-7 ]
  • [ 120-35-4 ]
  • 3-[3-(2-Methoxy-5-phenylcarbamoyl-phenyl)-thioureido]-benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethyl acetate; Example 113 3-[3-(2-Methoxy-5-phenylcarbamoyl-phenyl)-thioureido]-benzoic acid A mixture of 4-methoxy-3-amino-N-phenyl-benzamide (0.73 g, 3.0 mmol) and 3-carboxyphenyl isothiocyanate (0.54 g, 3.0 mmol) in ethyl acetate (60 mL) was warmed briefly to 50 C. and then allowed to stand overnight at room temperature. The mixture was then rewarmed to 50 C., filtered, and concentrated to dryness. Trituration of the residue in ethyl acetate followed by filtration afforded the product (1.083 g); m.p. 196-197 C. Calculated for C22H19N3O4S: C, 62.69; H, 4.54; N, 9.97. Found: C, 62.43; H, 4.55; N, 9.83.
  • 72
  • acetoxymandeloyl chloride [ No CAS ]
  • [ 120-35-4 ]
  • (2-methoxy-5-phenylcarbamoyl-phenylcarbamoyl)-acetic acid phenylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In ethyl acetate; Example 252 (2-Methoxy-5-phenylcarbamoyl-phenylcarbamoyl)-acetic acid phenylmethyl ester Acetoxymandeloyl chloride (1.10 g, 5 mmol) was added to a mixture of 4-methoxy-3-amino-N-phenyl-benzamide (1.24 g, 5 mmol) and triethylamine (1.25 mL, 9 mmol) in ethyl acetate (50 mL). The flask was agitated briefly then allowed to stand overnight at room temperature. The reaction mixture was diluted with ethyl acetate (150 mL), washed with aqueous sodium bicarbonate solution (150 mL) then brine (100 mL), dried over magnesium sulfate, and filtered. Removal of the solvent followed by trituration in hexanes/ethyl acetate (2:1) gave the product (1.46 g.); m.p. 168-171 C. Calculated for C24H22N2O5: C, 68.89; H, 5.30; N, 6.69. Found: C, 68.68; H, 5.14; N, 6.39.
  • 73
  • [ 98-31-7 ]
  • [ 120-35-4 ]
  • 3-(3,4-Dichloro-benzenesulfonylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; Example 136 3-(3,4-Dichloro-benzenesulfonylamino)-4-methoxy-N-phenyl-benzamide Prepared according to the procedure described for Example 121 using 3,4-dichlorobenzenesulfonyl chloride (2.45 g, 10 mmol), 3-amino-4-methoxy-N-phenyl-benzamide (2.43 g, 10 mmol) and pyridine (25 mL) to afford the product (4.183 g); m.p. 191-193 C. after trituration in hexanes/ethyl acetate (1:1).
  • 74
  • [ 120-35-4 ]
  • [ 2905-23-9 ]
  • 3-(2-Chloro-benzenesulfonylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; Example 127 3-(2-Chlorobenzenesulfonylamino)-4-methoxy-N-phenyl-benzamide Pyridine (5 mL) was added to a mixture of 3-amino-4-methoxy-N-phenyl-benzamide (0.73 g, 3.0 mmol) and 2-chlorobenzenesulfonyl chloride (0.63 g, 3.0 mmol) and stirred under an inert atmosphere at room temperature. After 20 hours, the mixture was diluted with water (50 mL) and acidified with conc. HCl. After 2 hours, the mixture was extracted with dichloromethane (2*50 mL). The combined extracts were washed successively with dilute aqueous HCl, water, and sat. brine then dried over MgSO4 and stripped of solvent under reduced pressure to afford the product (1.1 g); m.p. 107-109 C., after trituration in diethyl ether. Calculated for C20H17ClN2O4S.0.3 Ether: C, 57.99; H, 4.59; N, 6.38. Found: C, 57.86; H, 4.65; N, 6.16.
  • 75
  • [ 2888-06-4 ]
  • [ 120-35-4 ]
  • 3-(3-Chloro-benzenesulfonylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 123 3-(3-Chloro-benzenesulfonylamino)-4-methoxy-N-phenyl-benzamide Prepared according to the procedure described for Example 121 using 3-chlorobenzenesulfonyl chloride (2.27 g, 10 mmol) and 3-amino-4-methoxy-N-phenyl-benzamide (2.43 g, 10.0 mmol) to afford the product (3.846 g); m.p. 197-199 C. Calculated for C20H17ClN2O4S: C, 56.20; H, 4.01; N, 9.83. Found: C, 56.43; H, 4.10; N, 9.81.
  • 76
  • [ 2991-42-6 ]
  • [ 120-35-4 ]
  • 3-(4-Trifluoromethyl-benzenesulfonylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; In water; Example 128 3-(4-Trifluoromethyl-benzenesulfonylamino)-4-methoxy-N-phenyl-benzamide Pyridine (5 mL) was added to a mixture of 4-trifluoromethylbenzenesulfonyl chloride (0.73 g, 3.0 mmol) and 3-amino-4-methoxy-N-phenyl-benzamide (0.73 g, 3.0 mmol) and stirred at room temperature. After 20 hours, the mixture was added to water (50 mL), acidified with 2N HCl, and stirred for an hour. The precipitate was filtered off, rinsed with water, and dried to afford the product (1.2 g); m.p. 197-198 C. Calculated for C21H17F3N2O4S: C, 56.00; H, 3.80; N, 6.22. Found: C, 56.01; H, 3.85; N, 6.12.
  • 77
  • [ 1899-93-0 ]
  • [ 120-35-4 ]
  • 3-(Toluene-3-sulfonylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; Example 138 3-(Toluene-3-sulfonylamino)-4-methoxy-N-phenyl-benzamide Prepared according to the procedure described for Example 121 using 3-methylbenzenesulfonyl chloride (1.91 g, 10 mmol), 3-amino-4-methoxy-N-phenyl-benzamide (2.43 g, 10 mmol), and pyridine (25 mL) to afford the product (3.587 g); m.p. 195-197 C. after trituration in hexanes/ethyl acetate (1:1).
  • 78
  • [ 120-35-4 ]
  • [ 437-29-6 ]
  • 3-(4-Fluoro-phenylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 153 3-(4-Fluoro-phenylamino)-4-methoxy-N-phenyl-benzamide The title compound has been made using the procedure of Example 25, but using 3-amino-4-methoxy-N-phenyl benzamide (Aldrich) and tris(4-fluorophenyl)bismuthane as starting materials; m.p. 178-180 C.
  • 79
  • [ 120-35-4 ]
  • [ 100-83-4 ]
  • 3-(3-Hydroxy-benzylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 213 3-(3-Hydroxy-benzylamino)-4-methoxy-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 3-hydroxybenzaldehyde as starting materials, which are commercially available from Aldrich; m.p. 168-170 C.
  • 80
  • [ 32085-88-4 ]
  • [ 120-35-4 ]
  • 4-Methoxy-3-(3,5-difluoro-benzylamino)-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 267 4-Methoxy-3-(3,5-difluoro-benzylamino)-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 3,5-difluorobenzaldehyde as starting materials, which can be purchased from Aldrich; m.p. 175-177 C.
  • 81
  • [ 61652-81-1 ]
  • [ 120-35-4 ]
  • 3-(Decane-1-sulfonylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 179 3-(Decane-1-sulfonylamino)-4-methoxy-N-phenyl-benzamide The title compound has been made using the procedure of Example 128, but using 3-amino-4-methoxy-N-phenyl benzamide and 1-decanesulfonyl chloride as starting materials, which are commercially available from Aldrich and Lancaster; m.p. 160-161 C.
  • 82
  • [ 56946-83-9 ]
  • [ 120-35-4 ]
  • 3-(2,5-Dichloro-thiophene-3-sulfonylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 132 3-(2,5-Dichlorothiophene-3-sulfonylamino)-4-methoxy-N-phenyl-benzamide Prepared according to the procedure described for Example 127 using 2,5-dichlorothiophene-3-sulfonyl chloride (0.75 g, 3.0 mmol) and 3-amino-4-methoxy-N-phenyl-benzamide (0.73 g, 3.0 mmol) to afford the product (0.9 g); m.p. 189-190 C. Calculated for C18H14Cl2N2O4S2: C, 47.27; H, 3.09; N, 6.13. Found: C, 47.51; H, 3.04; N, 5.91.
  • 83
  • [ 120-35-4 ]
  • [ 122-03-2 ]
  • 3-(4-Isopropyl-benzylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 243 3-(4-Isopropyl-benzylamino)-4-methoxy-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 4-isopropylbenzaldehyde as starting materials, which are commercially available from Aldrich; m.p. 174-176 C.
  • 84
  • [ 120-35-4 ]
  • [ 621-30-7 ]
  • 4-Methoxy-N-phenyl-3-(3-m-tolyl-thioureido)-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 95 4-Methoxy-N-phenyl-3-(3-m-tolyl-thioureido)-benzamide Prepared according to the procedure described for Example 60 using 3-amino-4-methoxy-N-phenyl-benzamide (0.973 g, 4.00 mmol) and 3-methylphenyl isothiocyanate (0.55 mL, 4.07 mmol) to afford the product (0.305 g) in two crops; m.p. 168-117 C. Calculated for C22H21N3O2S.0.1 M H2O; C, 67.18; H, 5.43; N, 10.69. Found: C, 67.00; H, 5.32; N, 10.55.
  • 85
  • [ 120-35-4 ]
  • [ 532-55-8 ]
  • 3-[3-(3-Nitrophenyl)-thioureido]-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 254 4-Methoxy-3-[3-(3-nitro-phenyl)-thioureido]-N-phenyl-benzamide The title compound has been made using the procedure of Example 60, but using 3-amino-4-methoxy-N-phenyl benzamide and benzoyl isothiocyanate as starting materials, which are commercially available from Aldrich; m.p. 217-219 C.
  • 86
  • [ 120-35-4 ]
  • [ 532-55-8 ]
  • 4-Methoxy-N-phenyl-3-(3-benzoyl-thioureido)-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 67 4-Methoxy-N-phenyl-3-(3-benzoyl-thioureido)-benzamide Prepared according to the procedure described for Example 60 using 3-amino-4-methoxy-N-phenyl-benzamide (0.243 g, 1.0 mmol) and benzoyl isothiocyanate (0.171 g, 1.04 mmol) to afford the product (0.371 g); m.p. 219-222 C. CI Mass Spectrum: [M+H+]+=406. Calculated for C22H19N3O3S: C, 65.17; H, 4.72; N, 10.36. Found: C, 64.98; H, 4.57; N, 10.26.
  • 87
  • [ 705-21-5 ]
  • [ 120-35-4 ]
  • 3-(3,5-dichloro-benzenesulfonylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; Example 118 3-(3,5-Dichloro-benzenesulfonylamino)-4-methoxy-N-phenyl-benzamide Prepared according to the procedure described for Example 116 using 3-amino-4-methoxy-N-phenyl-benzamide (0.7296 g, 3.00 mmol), 3,5-dichlorobenzenesulfonyl chloride (0.7327 g, 3.00 mmol), and 4-dimethylaminopyridine to obtain the product (1.01 g); m.p. 222-228 C. Calculated for C20H16N2O4Cl2S: C, 53.23; H, 3.57; N, 6.21. Found: C, 53.23; H, 3.51; N, 6.11.
Example 248 3-(3,5-Dichloro-benzenesulfonylamino)-4-methoxy-N-phenyl-benzamide The title compound has been made using the procedure of Example 121, but using 3-amino-4-methoxy-N-phenyl benzamide and 3,5-dichlorophenylsulfonyl chloride as starting materials, which are commercially available from Aldrich or Lancaster; m.p. 226-228 C.
  • 88
  • [ 705-21-5 ]
  • [ 120-35-4 ]
  • 3-[Bis[(3,5-dichlorophenyl)sulfonyl]amino]-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 251 3-[Bis[(3,5-dichlorophenyl)sulfonyl]amino]-4-methoxy-N-phenyl-benzamide The title compound has been made using the procedure of Example 25, but using 3-amino-4-methoxy-N-phenyl benzamide and 3,5-dichlorophenylsulfonyl chloride as starting materials, which are commercially available from Aldrich or Lancaster; m.p. 228-231 C.
  • 89
  • [ 349-88-2 ]
  • [ 120-35-4 ]
  • 3-(4-Fluoro-benzenesulfonylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 125 3-(4-Fluoro-benzenesulfonylamino)-4-methoxy-N-phenyl-benzamide Prepared according to the procedure described for Example 121 using 4-fluorobenzenesulfonyl chloride (2.14 g 10 mmol) and 3-amino-4-methoxy-N-phenyl-benzamide (2.43 g, 10.0 mmol) to afford the product (3.522 g); m.p. 209-211 C. Calculated for C20H17FN2O4S: C, 59.99; H, 4.28; N, 7.00. Found: C, 59.96; H, 4.24; N, 6.87.
  • 90
  • [ 120-35-4 ]
  • [ 98-68-0 ]
  • 3-(4-Methoxy-benzenesulfonylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; In ethyl acetate; Example 121 3-(4-Methoxy-benzenesulfonylamino)-4-methoxy-N-phenyl-benzamide A mixture of 4-methoxybenzenesulfonyl chloride (2.21 g, 10.0 mmol), 3-amino-4-methoxy-N-phenyl-benzamide (2.43 g, 10.0 mmol) and pyridine (25 mL) was allowed to stand at room temperature until thin layer chromatography indicated the reaction to be complete. The mixture was then partitioned between water (400 mL) and ethyl acetate (400 mL). The layers were separated and the organic layer washed with water (2*400 mL), 1N HCL (100 mL), and brine (100 mL) dried (magnesium sulfate), filtered and stripped of solvent. Trituration of the residue in hexanes/ethyl acetate (1:1) and filtration afforded the product (3.754 g); m.p. 184-186 C. Calculated for C21H20N2O5S: C, 61.15; H, 4.89; N, 6.79. Found: C, 61.20; H, 5.03; N, 6.78.
  • 91
  • [ 2646-91-5 ]
  • [ 120-35-4 ]
  • 3-(2,3-Difluoro-benzylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 219 3-(2,3-Difluoro-benzylamino)-4-methoxy-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 2,3-difluorobenzaldehyde as starting materials, which are commercially available from Aldrich; m.p. 134-135 C.
  • 92
  • [ 23165-29-9 ]
  • [ 120-35-4 ]
  • 3-[3-(3,5-Bis-trifluoromethylphenyl)-thioureido]-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 89 3-[3-(3,5-Bis-trifluoromethylphenyl)-thioureido]-4-methoxy-N-phenyl-benzamide Prepared according to the procedure described for Example 60 using 3-amino-4-methoxy-N-phenyl-benzamide (0.972 g, 4.00 mmol) and 3,5-di(trifluoromethyl)phenyl isothiocyanate (1.08 g, 3.98 mmol) to afford the product (1.076 g); m.p. 192-193 C. Calculated for C23H17N3O2F6S: C, 53.80; H, 3.34; N, 8.18. Found: C, 53.71; H, 3.15; N, 8.15.
  • 93
  • [ 120-35-4 ]
  • [ 6590-93-8 ]
  • 3-[3-(3,5-dichlorophenyl)-thioureido]-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethyl acetate; Example 60 3-[3-(3,5-Dichlorophenyl)-thioureido]-4-methoxy-N-phenyl-benzamide A mixture of 3-amino-4-methoxy-N-phenyl-benzamide (0.277 g, 1.14 mmol) and 3,5-dichlorophenyl isothiocyanate (0.238 g, 1.17 mmol) in ethyl acetate (30 mL) was warmed until a solution was obtained, then allowed to stand at room temperature for 3 days. The reaction was concentrated until a crystalline precipitate was obtained then allowed to stand overnight at room temperature. The solid was collected by filtration, rinsed with ethyl acetate/hexane, and dried to afford the product (0.423 g); m.p. 195-197 C. Calculated for C21H17Cl2N3O2S: C, 56.51; H, 3.84; N, 9.41. Found: C, 56.20; H, 3.69; N, 9.28.
Same Skeleton Products
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