4949-69-3|4-Iodo-3-methylaniline| Ambeed

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Quality Control of [ 4949-69-3 ] Purity: 97% SDS Specification

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Product Details of [ 4949-69-3 ]

CAS No. :	4949-69-3
Formula :	C₇H₈IN
M.W :	233.05
SMILES Code :	NC1=CC=C(I)C(C)=C1
MDL No. :	MFCD01569451
InChI Key :	UISBOJCPTKUBIC-UHFFFAOYSA-N
Pubchem ID :	2734275

Safety of [ 4949-69-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 4949-69-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	9
Num. arom. heavy atoms	6
Fraction Csp3	0.14
Num. rotatable bonds	0
Num. H-bond acceptors	0.0
Num. H-bond donors	1.0
Molar Refractivity	48.53
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	26.02 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.78
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.13
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.19
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.72
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.55
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.28

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.12
Solubility	0.177 mg/ml ; 0.000758 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.31
Solubility	1.15 mg/ml ; 0.00492 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.38
Solubility	0.0965 mg/ml ; 0.000414 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.21 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	2.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.45

Application In Synthesis of [ 4949-69-3 ]

* 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 [ 4949-69-3 ]

[ 4949-69-3 ] Synthesis Path-Downstream 1~41

1
[ 21368-28-5 ]
[ 4949-69-3 ]
N-(4-chloro-phenyl)-N'-(4-iodo-3-methyl-phenyl)-urea [ No CAS ]

References: [1]Journal of the Chinese Chemical Society (Peking),1946,vol. 13,p. 22,26,27.
Recueil des Travaux Chimiques des Pays-Bas,1940,vol. 59,p. 231,233,234.
[2]Journal of the Chinese Chemical Society (Peking),1946,vol. 13,p. 22,26,27.
Recueil des Travaux Chimiques des Pays-Bas,1940,vol. 59,p. 231,233,234.

2
[ 14917-59-0 ]
[ 4949-69-3 ]
N-(4-bromo-phenyl)-N'-(4-iodo-3-methyl-phenyl)-urea [ No CAS ]

3
[ 50625-49-5 ]
[ 4949-69-3 ]
N-(3-chloro-phenyl)-N'-(4-iodo-3-methyl-phenyl)-urea [ No CAS ]

4
[ 72755-05-6 ]
[ 4949-69-3 ]
N-(3-bromo-phenyl)-N'-(4-iodo-3-methyl-phenyl)-urea [ No CAS ]

5
[ 2733-41-7 ]
[ 4949-69-3 ]
N-(4-iodo-3-methyl-phenyl)-N'-(4-nitro-phenyl)-urea [ No CAS ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1940,vol. 59,p. 231,235.
Journal of the Chinese Chemical Society (Peking),1946,vol. 13,p. 28,35,40,42,45,47.

6
[ 537-92-8 ]
[ 4949-69-3 ]

References: [1]American Chemical Journal,1910,vol. 44,p. 131.
Chemisches Zentralblatt,1910,vol. 81,p. 877.

7
[ 1134-10-7 ]
[ 4949-69-3 ]
N-(4-iodo-3-methyl-phenyl)-N'-(2-nitro-phenyl)-urea [ No CAS ]

8
[ 5326-38-5 ]
[ 4949-69-3 ]

References: [1]RSC Advances,2015,vol. 5,p. 34398 - 34414.
[2]Recueil des Travaux Chimiques des Pays-Bas,1912,vol. 31,p. 271.
[3]Monatshefte fur Chemie,1905,vol. 26,p. 1103.
[4]Journal of the Chemical Society,1922,vol. 121,p. 677.
[5]Journal of the Chemical Society,1922,vol. 121,p. 677.

9
[ 3532-31-8 ]
[ 4949-69-3 ]
N-(4-iodo-3-methyl-phenyl)-N'-(3-nitro-phenyl)-urea [ No CAS ]

10
[ 6633-29-0 ]
[ 4949-69-3 ]
N-(4-iodo-3-methyl-phenyl)-N'-(4-methyl-3,5-dinitro-phenyl)-urea [ No CAS ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1939,vol. 58,p. 1008,1010.
Recueil des Travaux Chimiques des Pays-Bas,1940,vol. 59,p. 231,234.

11
[ 4949-69-3 ]
[ 49747-51-5 ]
N-(2-chloro-phenyl)-N'-(4-iodo-3-methyl-phenyl)-urea [ No CAS ]

12
[ 590-28-3 ]
[ 4949-69-3 ]
(4-iodo-3-methyl-phenyl)-urea [ No CAS ]

References: [1]Monatshefte fur Chemie,1905,vol. 26,p. 1103.

13
[ 4949-69-3 ]
[ 117832-10-7 ]

References: [1]American Chemical Journal,1910,vol. 44,p. 131.
Chemisches Zentralblatt,1910,vol. 81,p. 877.

14
[ 4949-69-3 ]
[ 108-24-7 ]
[ 97113-39-8 ]

References: [1]Monatshefte fur Chemie,1905,vol. 26,p. 1103.
[2]Advanced Synthesis and Catalysis,2005,vol. 347,p. 1921 - 1924.

15
[ 4949-69-3 ]
[ 100-28-7 ]
N-(4-iodo-3-methyl-phenyl)-N'-(4-nitro-phenyl)-urea [ No CAS ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1940,vol. 59,p. 231,235.
Journal of the Chinese Chemical Society (Peking),1946,vol. 13,p. 28,35,40,42,45,47.

16
[ 100377-05-7 ]
[ 108-44-1 ]
[ 4949-69-3 ]

References: [1]Zhurnal Obshchei Khimii,1956,vol. 26,p. 3139,3143; engl. Ausg. S. 3499, 3503.

17
[ 108-44-1 ]
[ 4949-69-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With 1,4-dibenzyl-1,4-diazoniabicyclo[2.2.2]octane dichloroiodate; In neat (no solvent); at 20℃; for 0.25h;	General procedure: General procedure for the iodination of aryl amines under solvent-free conditions.DBDABCODCI (0.5 mmol) and aryl amine (1 mmol) were triturated together in a porcelainmortar at room temperature. After completing reaction which monitored by TLC, the ethylacetate added to mixture and filtered, the organic layer washed with 5% aqueous sodiumthiosulfate, and dried over MgSO4. The solvent was removed in vacuum and the crude mixturewas purified by column chromatography using ethyl acetate and hexane mixture and analyzedby m.p. and 1H NMR spectroscopy.
70%	With iodine; sodium carbonate; In cyclohexane; water; at 20℃; for 0.5h;	General procedure: To a clean 50 mL round bottomed flask equipped with a large stir bar was added the substrate (10 mmol) followed by cyclohexane (ca. 6.0 mL to maintain the reaction concentration of 1.67 M) and an aqueous saturated solution of sodium carbonate (2.8 mL). Finally, iodine beads (11 mmol) were added as a solid and the flask was sealed with a septum and vented with a needle to the open atmosphere. The reaction was allowed to stir for the specified time at room temperature unless otherwise noted (see refPreviewPlaceHolderTable 1). The reaction mixture was poured into a separatory funnel with the aid of ethyl acetate or MTBE (2-3 mL) with additional aqueous saturated sodium carbonate (1 mL). The organic layer was washed twice with an aqueous saturated solution of sodium bisulfite (4 mL) and brine (5 mL), dried over sodium sulfate, and concentrated in vacuo to provide crude iodinated product. The products were purified by crystallization (if crystalline) from hexanes. Column chromatography (ethyl acetate/hexanes) was performed on the oils.

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 8622 - 8624.
[2]Bulletin of the Chemical Society of Ethiopia,2015,vol. 29,p. 157 - 162.
[3]New Journal of Chemistry,2019,vol. 43,p. 6001 - 6009.
[4]Bulletin of the Chemical Society of Japan,1988,vol. 61,p. 600 - 602.
[5]Journal of the Chinese Chemical Society,1996,vol. 43,p. 95 - 99.
[6]Molecules,2004,vol. 9,p. 617 - 621.
[7]Tetrahedron Letters,2011,vol. 52,p. 7141 - 7145.
[8]American Chemical Journal,1910,vol. 44,p. 131.
Chemisches Zentralblatt,1910,vol. 81,p. 877.

18
[ 4949-69-3 ]
[ 4023-34-1 ]
[ 23745-35-9 ]

References: [1]Patent: DE1803084,1969, .
Chem.Abstr.,1969,vol. 71.

19
[ 60-29-7 ]
[ 7732-18-5 ]
[ 108-44-1 ]
iodine (1.5 mol) [ No CAS ]
calcium carbonate [ No CAS ]
[ 4949-69-3 ]
[ 117832-10-7 ]

References: [1]American Chemical Journal,1910,vol. 44,p. 131.
Chemisches Zentralblatt,1910,vol. 81,p. 877.

21
[ 7664-93-9 ]
[ 4949-69-3 ]
[ 7553-56-2 ]

References: [1]American Chemical Journal,1910,vol. 44,p. 131.
Chemisches Zentralblatt,1910,vol. 81,p. 877.

22
[ 7647-01-0 ]
[ 64-17-5 ]
[ 4949-69-3 ]
tin (II)-chloride [ No CAS ]
[ 7553-56-2 ]

References: [1]Journal of the Chemical Society,1922,vol. 121,p. 677.

23
[ 5326-38-5 ]
[ 4949-69-3 ]
[ 108-44-1 ]

References: [1]Synthesis,2003,p. 1657 - 1660.

24
[ 4949-69-3 ]
[ 75-36-5 ]
[ 97113-39-8 ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 8127 - 8134.

25
[ 4949-69-3 ]
[ 98-59-9 ]
N-(4-iodo-3-methylphenyl)-4-methylbenzenesulfonamide [ No CAS ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 13148 - 13149.
[2]Organic Letters,2015,vol. 17,p. 2222 - 2225.

26
[ 55477-80-0 ]
[ 4949-69-3 ]
3-(4-amino-2-methylphenyl)-2-tert-butoxycarbonylaminoacrylic acid methyl ester [ No CAS ]

References: [1]Synthesis,2006,p. 1183 - 1189.

27
[ 4949-69-3 ]
[ 623907-55-1 ]

Yield	Reaction Conditions	Operation in experiment
29%		3-Thiophenecarboxylic acid (2.0 g, 15.6 mmol) was dissolved in methylene chloride (100 rnL) and 2 drops of DMF were added. The mixture was cooled to about 0 0C and oxalyl chloride (1.5 mL, 17.1 mmol) was added slowly and allowed to warm to room temperature. Gas evolution was observed during warming. 3-Methyl-4-iodoaniline (5.45 g, 23.5 mmol), 4 drops of pyridine and K2CO3 (2.58 g, 18.7 mmol) are dissolved in CH2Cl2 (10 mL) and cooled to about 0 0C. After about Ih, the acid chloride mixture is slowly added to the cooled aniline mixture and allowed to warm to room temperature and stirred for about 18h. The resulting mixture is filtered, washed with ethyl acetate and the filtrate is concentrated to a brown oil. The crude material was purified via flash chromatography (10-30% ethyl acetate in hexanes) to afford the desired product (1.56 g, 29%) as an off-white solid.

References: [1]Patent: WO2007/147103,2007,A2 .Location in patent: Page/Page column 131.

28
[ 88-13-1 ]
[ 4949-69-3 ]
[ 623907-55-1 ]

Yield	Reaction Conditions	Operation in experiment
29%	With oxalyl dichloride; potassium carbonate;pyridine; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃; for 19h;	3-Thiophenecarboxylic acid (2.0 g, 15.6 mmol) was dissolved in methylene chloride (100 mL) and 2 drops of DMF were added. The mixture was cooled to 0 0C and oxalyl chloride (1.5 mL, 17.1 mmol) was added slowly and allowed to warm to room temperature. Gas evolution was observed during warming. 3-Methyl-4-iodoaniline (5.45 g, 23.5 mmol), 4 drops of pyridine and K2CO3 (2.58 g, 18.7 mmol) are dissolved in CH2Cl2 (10 mL) and <n="112"/>cooled to about 0 0C. After about Ih, the acid chloride mixture is slowly added to the cooled aniline mixture and allowed to warm to room temperature and stirred for about 18h. The resulting mixture is filtered, washed with ethyl acetate and the filtrate is concentrated to a brown oil. The crude material was purified via flash chromatography (10-30% ethyl acetate in hexanes) to afford the title compound (1.56 g, 29%) as an off-white solid.

References: [1]Patent: WO2007/147109,2007,A2 .Location in patent: Page/Page column 110-111.

29
[ 4949-69-3 ]
[ 867309-17-9 ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 13148 - 13149.
[2]Organic Letters,2015,vol. 17,p. 2222 - 2225.

30
[ 4949-69-3 ]
butyl (E)-3-[2-(acetylamino)-4-methyl-5-iodophenyl]-2-propenoate [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2005,vol. 347,p. 1921 - 1924.

31
[ 4949-69-3 ]
[ 89641-12-3 ]

References: [1]American Chemical Journal,1910,vol. 44,p. 131.
Chemisches Zentralblatt,1910,vol. 81,p. 877.

32
[ 4949-69-3 ]
[ 89975-84-8 ]

References: [1]American Chemical Journal,1910,vol. 44,p. 131.
Chemisches Zentralblatt,1910,vol. 81,p. 877.

33
[ 4949-69-3 ]
acetic acid-(2,4-diiodo-5-methyl-anilide) [ No CAS ]

References: [1]American Chemical Journal,1910,vol. 44,p. 131.
Chemisches Zentralblatt,1910,vol. 81,p. 877.

34
[ 4949-69-3 ]
acetic acid-(2,4,6-triiodo-3-methyl-anilide) [ No CAS ]

References: [1]American Chemical Journal,1910,vol. 44,p. 131.
Chemisches Zentralblatt,1910,vol. 81,p. 877.

35
[ 4949-69-3 ]
N-acetyl-N'-(4-iodo-3-methyl-phenyl)-urea [ No CAS ]

References: [1]Monatshefte fur Chemie,1905,vol. 26,p. 1103.

36
[ 4949-69-3 ]
(2E)-2-cyano-2-[(4-iodo-3-methylphenyl)hydrazono]acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		[00696] Example 8: 4-[(aminocarbonyl) amino]-1-(4-iodo-3- methylphenyl)-1 H-pyrazole-3-carboxamide; [00698] Step 1: Preparation of (2E)-2-cyano-2- [ (4-iodo-3- methylphenyl) hydrazono] acetamide; [00700] A mechanically stirred slurry of <strong>[4949-69-3]3-methyl-4-iodoaniline</strong> (23.3 g, 0.1 mole) and concentrated HCI (25 mL) in water (80 mL) was cooled to 5C and a cold solution of sodium nitrite (6.9 g, 0.1 mole, dissolved in 20 mL water) was added slowly over a period of 30 min. , maintaining the reaction temperature at 0-5C. A solution of sodium acetate trihydrate (40.8 g, 0.3 mole) in water (100 mL) was then added dropwise over 15-30 min. [00701] This mixture was then slowly added to a cold (5C) mechanically stirred solution of sodium cyanoacetamide [previously prepared by the dissolution of cyanoacetamide (12.6 g, 0.15 mol) in cold (5C) water (150 mL)/ethanol (100 mL) followed by the addition of a cold solution of sodium acetate trihydrate (13.6 g, 0.1 mol) in water (30 mL) ] over a period of 30 min. A thick brown slurry was obtained which was stirred for three additional hours in a wet ice bath. The slurry was filtered and the solids washed with water (200 mL). The material was dried in vacuo to give a reddish brown solid.'H NMR (300 MHz, DMSO-d6) : 5 8.13 (s,-1 H), 8.07-7. 98 (m, 3 H), 7.81 (s, 1 H), 7. 5-0 (d, J = 8.3 Hz, 1 H), 2.65 (s, 3 H). MS (ESI-) for CroHgIN4O m/z 327 (M-H)-.

References: [1]Patent: WO2005/37797,2005,A1 .Location in patent: Page/Page column 199-200.

37
[ 4949-69-3 ]
[ 87-13-8 ]
[ 797041-92-0 ]

Yield	Reaction Conditions	Operation in experiment
	at 130℃; for 2.5h;	4-lodo-3-methylaniline (5.75 g) was suspended in diethyl ETHOXYMETHYLENEMALONATE (5.5 mL). The mixture was heated at 130oC for 2.5 h. After cooling to-90oC, hexane was added and the mixture stirred while cooling to room temperature. The product crystallised out, and was filtered off, washing well with more hexane. The solid was dried in vacuo to yield the title compound as a pale grey powder (7.947 g) ; 1 H NMR 8 (CDCI3) 1.33 (3H, t), 1.38 (3H, t), 2.43 (3H, s), 4.25 (2H, q), 4.3 (2H, q), 6.69 (1 H, dd), 7.01 (1 H, d), 7.75 (1 H, d), 8.46 (1 H, d), and 10.95 (1 H, br d).

References: [1]Patent: WO2004/101586,2004,A1 .Location in patent: Page 41.

38
[ 4949-69-3 ]
[ 329-01-1 ]
[ 1239985-86-4 ]

Yield	Reaction Conditions	Operation in experiment
	In benzene; at 90℃; for 4h;	To a solution of <strong>[4949-69-3]4-iodo-3-methylaniline</strong> (200 mg, 0.86 mmol) in benzene (5 mL) in a sealable tube was added 1- isocyanato-3- (trifluoromethyl)benzene (0.133 mL, 0.94 mL; "E" is an electrophilic group disussed in scheme 3, and here is an isocyanate) . The tube was sealed and heated at 90 C for 4 h. The mixture was allowed to cool to room temperature before filtering. The off white solid was washed with additional benzene (10 mL) and used without further purification.

References: [1]Patent: WO2006/44823,2006,A2 .Location in patent: Page/Page column 120.

39
[ 4949-69-3 ]
[ 2251-65-2 ]
[ 1239985-85-3 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 0.5h;	To a solution of 4-iodo-3-methyl aniline (200 mg, 0.86 mmol) and iPr2NEt (0.19 mL, 0.95 mmol) in CH2Cl2 (10 itiL) was added 3- (trifluoromethyl)benzoyl chloride (0.133 mL, 0.90 mmol) . The mixture was allowed to stir at room temperature for 0.5 h at which time it was diluted with CH2Cl2 (20 mL) . The organic layer was washed with aq. HCl (10 mL, 1 M) , 9% aq. Na2CO3 (10 mL) , brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting oil was used without further purification.

References: [1]Patent: WO2006/44823,2006,A2 .Location in patent: Page/Page column 118.

40
[ 41507-35-1 ]
[ 4949-69-3 ]
[ 623907-55-1 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; potassium carbonate; In dichloromethane; at 0 - 20℃; for 19h;	Example 7; N-(3-{8-(2.6-DifluorophenylV7-oxo-2-r(2,2,6.6-tetramethyl-4-piperidinyl')aminol-5,6,7, 8-tetrahydropyrimido[4,5-(/1pyrimidin-4-yl\|-4-methylphenyl)-3- thiophenecarboxamide; 7a) N-Q -iodo-4-methyrphenyl)-3 -thiophenecarboxamide; 3-Thiophenecarboxylic acid (2.O g, 15.6 mmol) was dissolved in methylene chloride (100 mL) and 2 drops of DMF were added. The mixture was cooled to 0 0C and oxalyl chloride (1.5 mL, 17.1 mmol) was added slowly and allowed to warm to room temperature. Gas evolution was observed during warming. 3-Methyl-4- iodoaniline (5.45 g, 23.5 mmol), 4 drops of pyridine and K2CO3 (2.58 g, 18.7 mmol) are dissolved in CH2Cl2 (10 mL) and cooled to about 00C. After about Ih, the acid chloride mixture is slowly added to the cooled aniline mixture and allowed to warm to room temperature and stirred for about 18h. The resulting mixture is filtered, washed with ethyl acetate and the filtrate is concentrated to a brown oil. The crude EPO <DP n="125"/>material was purified via flash chromatography (10-30% ethyl acetate in hexanes) to afford the title compound (1.56 g, 29%) as an off-white solid.

References: [1]Patent: WO2006/104889,2006,A2 .Location in patent: Page/Page column 123-124.

41
[ 4949-69-3 ]
[ 630120-96-6 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 271A 2-bromo-N-(4-iodo-3-methylphenyl)acetamide The procedure described in Example 1A was followed, substituting <strong>[4949-69-3]4-iodo-3-methylaniline</strong> for 3-methylaniline to provide the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) delta 2.33 (s, 3H), 4.02 (s, 2H), 7.20 (dd, 1H, J=8.5, 2.4 Hz), 7.56 (d, 1H, J=2.4 Hz), 7.74 (d, 1H, J=8.5 Hz), 10.40 (br s, 1H); MS (DCI/NH3) m/e 353/355 (M+H)+; 371.373 (M+NH4)+.

References: [1]Patent: US2004/29887,2004,A1 .

Historical Records

Technical Information

• Alkyl Halide Occurrence • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Friedel-Crafts Reaction • General Reactivity • Hiyama Cross-Coupling Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Kinetics of Alkyl Halides • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Alkylbenzene • Preparation of Amines • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Dihalides • Specialized Acylation Reagents-Vilsmeier Reagent • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Ugi Reaction • Vilsmeier-Haack Reaction

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CAS No.: 4949-69-3

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CAS No.: 4949-69-3

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