[ CAS No. 3400-22-4 ]

Name: 3400-22-4|4-Methoxy-N-methylbenzamide|96%
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Quality Control of [ 3400-22-4 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 3400-22-4 ]

CAS No. :	3400-22-4	MDL No. :	MFCD00522600
Formula :	C₉H₁₁NO₂	Boiling Point :	322.7°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	165.19 g/mol	Pubchem ID :	346031
Synonyms :

Calculated chemistry of of [ 3400-22-4 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	45.93
TPSA :	38.33 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.6 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.91
Log Po/w (XLOGP3) :	1.0
Log Po/w (WLOGP) :	1.05
Log Po/w (MLOGP) :	1.23
Log Po/w (SILICOS-IT) :	1.38
Consensus Log Po/w :	1.31

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.67
Solubility :	3.56 mg/ml ; 0.0216 mol/l
Class :	Very soluble
Log S (Ali) :	-1.39
Solubility :	6.67 mg/ml ; 0.0404 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.9
Solubility :	0.206 mg/ml ; 0.00125 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 3400-22-4 ]

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 [ 3400-22-4 ]

* 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 [ 3400-22-4 ]

[ 3400-22-4 ] Synthesis Path-Downstream 1~32

1
[ 100-07-2 ]
[ 74-89-5 ]
[ 3400-22-4 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; water; at 0 - 20℃; for 1h;	General procedure: Triethylamine (15 mmol), 33.3% methylamine in water (20 mmol) were added tothe solution of acid chloride (10 mmol) in CH2Cl2 (20 mL) at 0C. The reactionmixture was stirred at room temperature for 1 h and monitored by TLC until thereaction was completed. Then water (50 mL) was added to the mixture and extractedwith CH2Cl2 (30 mL). The organic phase was dried over anhydrous Na2SO4 andconcentrated under reduced pressure. The residue can be purified by silica gel flashchromatography or recrystallization, and the corresponding benzamide products canbe obtained with a yield of 80-95%.

Reference： [1]Journal of the Chemical Society,1926,p. 2414
[2]Journal of Physical Chemistry,1987,vol. 91,p. 1247 - 1251
[3]Journal of Organic Chemistry,2008,vol. 73,p. 2428 - 2431
[4]Journal of the American Chemical Society,2013,vol. 135,p. 4628 - 4631
[5]Organic Letters,2015,vol. 17,p. 3714 - 3717
[6]Journal of Organic Chemistry,2017,vol. 82,p. 3622 - 3630
[7]Organic Letters,2017,vol. 19,p. 4223 - 4226
[8]Angewandte Chemie - International Edition,2019,vol. 58,p. 13039 - 13043
Angew. Chem.,2019,vol. 131,p. 13173 - 13177,5
[9]Organic Letters,2019,vol. 21,p. 6259 - 6263
[10]Journal of Organic Chemistry,2019,vol. 84,p. 11823 - 11838
[11]Chinese Chemical Letters,2022,vol. 33,p. 1541 - 1544
[12]Synthesis,2022

2
[ 696-63-9 ]
[ 201230-82-2 ]
[ 622-29-7 ]
[ 98098-60-3 ]
[ 68162-88-9 ]
[ 3400-22-4 ]

Reference： [1]Canadian Journal of Chemistry,1986,vol. 64,p. 2010 - 2012

3
[ 13214-64-7 ]
[ 3400-22-4 ]

Reference： [1]Synthesis,1982,p. 141 - 143

4
[ 5335-05-7 ]
[ 3400-22-4 ]
[ 134814-88-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1991,p. 563 - 570

5
[ 3400-22-4 ]
[ 132606-41-8 ]

Reference： [1]Acta Chimica Hungarica,1990,vol. 127,p. 439 - 450

6
[ 3400-22-4 ]
[ 78554-86-6 ]

Yield	Reaction Conditions	Operation in experiment
11.9 g (76%)	With thionyl chloride;	EXAMPLE I N-Methyl 4-Methoxybenzimidoyl Chloride N-Methyl 4-methoxybenzamide (13.95 g, 84.5 mmole) was placed in a 50 ml round bottom flask equipped with magnetic stirrer, heating mantle, condenser and base trap. Thionyl chloride (33 g, 278 mmole) was added. The reaction was stirred and heated at reflux until gas evolution ceased (three hours). The excess thionyl chloride was distilled at ca. 15 mm Hg, and the product distilled at 75-80 C. (0.1 mm Hg) to yield 11.9 g (76%) of the title compound as a clear colorless liquid.

Reference： [1]Journal of Organic Chemistry,1984,vol. 49,p. 546 - 547
[2]Patent: US4528382,1985,A
[3]Chemical Communications,2013,vol. 49,p. 5313 - 5315

7
[ 3400-22-4 ]
[ 100-09-4 ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 710 - 711

8
[ 84-51-5 ]
[ 3400-22-4 ]
C₃₂H₂₄O₆ [ No CAS ]

Reference： [1]Synthetic Communications,2000,vol. 30,p. 803 - 820

9
[ 86-81-7 ]
[ 3400-22-4 ]
[ 212501-06-9 ]

Reference： [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 2204 - 2218

10
[ 2186-24-5 ]
[ 3400-22-4 ]
2-(2-hydroxy-3-<i>p</i>-tolyloxy-propyl)-4-methoxy-<i>N</i>-methyl-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-methoxy-N-methylbenzamide With n-butyllithium In tetrahydrofuran; diethyl ether at 20℃; for 0.5h; Stage #2: cresyl-glicidyl ether In tetrahydrofuran; diethyl ether at -15 - 20℃;

Reference： [1]Brahmbhatt; Pandya, Urvish R. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 9, p. 2100 - 2103]

11
[ 93-89-0 ]
[ 3400-22-4 ]
[ 919475-63-1 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6954 - 6957

12
[ 3400-22-4 ]
2-{3-hydroxy-2-[(pyridin-3-ylmethyl)amino]propyl}-6-methoxy-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6954 - 6957

13
[ 3400-22-4 ]
2-(2-amino-3-diphenylsilanyloxy-propyl)-6-methoxy-1-oxo-4-phenyl-1,2-dihydro-isoquinoline-3-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6954 - 6957

14
[ 100-07-2 ]
[ 3400-22-4 ]

Yield	Reaction Conditions	Operation in experiment
		a. 4-Methoxy-N-methylbenzamide. Using a procedure similar to that described in Example 28 sub-part a, except replacing 2-methoxybenzoyl chloride with 4-methoxybenzoyl chloride (10 g) the amide was prepared (7.22 g) as a solid: mp 111-113 C.; MS: m/z=166; NMR(CDCl3): 3.0 (d, J=4.9, 3), 3.84 (s,3), 6.90 (m,2), 7.74 (m,2).
	With dimethyl amine; In dichloromethane;	EXAMPLE 1 4-Methoxy-N-methyl-benzamide (8) An addition funnel containing p-anisoyl chloride (47.6 g, 279 mmol) and methylene chloride (125 mL) was attached to a 2L 3-neck round bottom flask containing 375 mL methylene chloride. The reaction flask was cooled in an ice bath and methylamine (g) was bubbled through the solvent. The contents of the addition funnel were added dropwise. A white precipitate appeared. Warmed to room temperature and stirred for 24 h. Washed with water; separated layers and dried the organic portion with sodium sulfate (anh.). Removal of the solvent in vacuo followed by trituration with hexane/ether gave 8 as a white solid (33.7 g, 204 mmol, 73.2%) 1H-NMR (CHCl3, 300 MHz) δ 7.80 (d, 2H); 6.95 (d, 2H); 6.10 (s, br, 1H); 3.85 (s, 3H), 3.00 (d, 3H).

Reference： [1]Patent: US5589489,1996,A
[2]Patent: US2004/44030,2004,A1
[3]Tetrahedron Letters,2015,vol. 56,p. 6227 - 6230
[4]Organic Letters,2020,vol. 22,p. 4583 - 4587
[5]Structural Chemistry,2021,vol. 32,p. 1077 - 1091
[6]Structural Chemistry,2021,vol. 32,p. 1077 - 1091
[7]Structural Chemistry,2021,vol. 32,p. 1077 - 1091

15
[ 3400-22-4 ]
[ 92753-20-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sec.-butyllithium; benzaldehyde; In tetrahydrofuran; toluene;	EXAMPLE 3 5-Methoxy-3-phenyl-3H-isobenzofuran-1-one (9) A solution of 8 (15 g, 91 mmol) in THF was cooled to -70 C. under Argon. To this was added sec-butyllithium (147 mL, 1.3M). After stirring 0.5 h a tan suspension resulted. Added benzaldehyde (9.2 mL, 91 mmol.) and stirred 1 h. Quenched with ice then removed TiF in vacuo. Added sat. sodium bicarbonate and extracted with ethyl acetate (4*). Dried the combined organic portions with sodium sulfate (anh.) and removed the solvent in vacuo. Added toluene and heated to reflux for 1 h. Removal of the solvent in vacuo followed by trituration with hexane/ether gave unreacted starting material 8 (4.63 g). Concentration of the filtrate in vacuo followed by flash column chromatography (hexane:ethyl acetate 80:20) gave 9 as a yellow solid (12.0 g, 50.1 mmol, 55.1%) 1H-NMR(CHCl3, 300MHz) δ 7.90 (d, 1H); 7.40-7.20 (m, 4H); 7.05 (d, 1H); 6.75 (s, 1H), 6.30 (s, 1H); 3.82 (s, 3H).

Reference： [1]Patent: US2004/44030,2004,A1

16
[ 52898-49-4 ]
[ 3400-22-4 ]

Yield	Reaction Conditions	Operation in experiment
96%	With sodium metal trapped in the nanoscale pores of silica gel; In tetrahydrofuran; at 20℃; for 2h;Glovebox; Sealed tube; Inert atmosphere;	General procedure: In a helium-filled glove box, the desired number ofequivalents of Na-AG or Na-SG were added to a round bottom flask, along with aglass-coated stir bar, and the flask sealed with a septum. This closed systemwas then taken out of the glove box, continuously purged with nitrogen, followedby injection of the pure synthesized Weinreb amide dissolved in THF. The resulting mixture was stirred for thetime specified. After completion of the reaction, the mixture was then partitioned using ethyl acetate and brine. The organic layer was concentrated under reducedpressure using a rotary evaporator. 1H NMR of the crude product wastaken to check for reaction extent/completion and to identify the productsobtained. Crude product was fractionated and purified by columnchromatography on silica gel to afford the desired product and byproducts.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 6227 - 6230
[2]Synlett,2008,p. 2132 - 2136
[3]Journal of Organic Chemistry,2017,vol. 82,p. 6528 - 6540

17
[ 372-48-5 ]
[ 52898-49-4 ]
[ 79574-74-6 ]
[ 3400-22-4 ]

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 781 - 784

18
[ 123-39-7 ]
[ 104-92-7 ]
[ 3400-22-4 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 6358 - 6361

19
[ 593-51-1 ]
[ 100-07-2 ]
[ 3400-22-4 ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 10565 - 10569
[2]Chemical Communications,2011,vol. 47,p. 12074 - 12076
[3]Organic and Biomolecular Chemistry,2012,vol. 10,p. 9429 - 9439
[4]Angewandte Chemie - International Edition,2013,vol. 52,p. 13086 - 13090
Angew. Chem.,2013,vol. 125,p. 13324 - 13328,5
[5]Journal of Organic Chemistry,2016,vol. 81,p. 6056 - 6065
[6]Organic and Biomolecular Chemistry,2017,vol. 15,p. 7330 - 7338
[7]Angewandte Chemie - International Edition,2020,vol. 59,p. 15076 - 15080
Angew. Chem.,
[8]Chemical Communications,2021,vol. 57,p. 8917 - 8920

20
[ 501-65-5 ]
[ 3400-22-4 ]
[ 1235478-87-1 ]

Yield	Reaction Conditions	Operation in experiment
42%	With sodium iodide dihydrate; palladium 10% on activated carbon; potassium acetate; caesium carbonate; In N,N-dimethyl-formamide; at 140℃; for 36h;Schlenk technique;	General procedure: A mixture of a substituted benzamide (1) (0.3 mmol, 1.0 equiv),an alkyne (2) (0.6 mmol or 0.9 mmol, 2.0 equiv or 3.0 equiv),10% Pd/C (0.03 mmol, 10 mol%, Alfa Aesar, No. 044696, eggshell,reduced), NaI·2H2O (0.6 mmol, 2.0 equiv), Cs2CO3 (0.3 mmol, 1.0equiv), and KOAc (0.6 mmol, 2.0 equiv) was weighted in a Schlenktube equipped with a stir bar. DMF (1.0 mL) was added and themixture was stirred at 120 C for 36 h under air. Afterwards, themixture was filtered and washed with H2O (30 mL) and extractedwith CH2Cl2 (3×30 mL). The combined organic phase was driedwith anhydrous Na2SO4. After removal of solvents under reducedpressure, the residue was absorbed to small amounts of silica. Thepurification was performed by flash column chromatography onsilica gel with EA:PE (Petroleum ether) = 1:5 or 1:10 as eluent.

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 10565 - 10569
[2]Green Chemistry,2017,vol. 19,p. 3219 - 3224
[3]Angewandte Chemie - International Edition,2011,vol. 50,p. 6379 - 6382
[4]Organic and Biomolecular Chemistry,2012,vol. 10,p. 9429 - 9439
[5]Catalysis Today,2017,vol. 297,p. 292 - 297

21
[ 104-92-7 ]
[ 14040-11-0 ]
[ 6638-79-5 ]
[ 52898-49-4 ]
[ 3400-22-4 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 978 - 981

22
[ 111-66-0 ]
[ 3400-22-4 ]
[ 1281888-64-9 ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 5221 - 5223

23
[ 2386-64-3 ]
[ 3400-22-4 ]
[ 1379242-86-0 ]
[ 1309375-45-8 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 3232 - 3234

24
[ 701-49-5 ]
[ 501-65-5 ]
[ 3400-22-4 ]
[ 1235478-87-1 ]
[ 1315257-13-6 ]

Yield	Reaction Conditions	Operation in experiment
	With [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; copper(II) acetate monohydrate In tert-Amyl alcohol at 100℃; for 22h; Inert atmosphere;

Reference： [1]Ackermann, Lutz; Lygin, Alexander V.; Hofmann, Nora [Angewandte Chemie - International Edition, 2011, vol. 50, # 28, p. 6379 - 6382]

25
[ 201230-82-2 ]
[ 3400-22-4 ]
[ 63196-45-2 ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 12074 - 12076

26
[ 100-09-4 ]
[ 3400-22-4 ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 12074 - 12076
[2]Journal of the American Chemical Society,2013,vol. 135,p. 4628 - 4631
[3]Angewandte Chemie - International Edition,2013,vol. 52,p. 13086 - 13090
Angew. Chem.,2013,vol. 125,p. 13324 - 13328,5
[4]Organic Letters,2019,vol. 21,p. 6259 - 6263
[5]Angewandte Chemie - International Edition,2020,vol. 59,p. 15076 - 15080
Angew. Chem.,
[6]Synlett,2021

27
[ 140-88-5 ]
[ 3400-22-4 ]
[ 1355020-64-2 ]
[ 1355020-74-4 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 728 - 731

28
[ 3400-22-4 ]
[ 98-80-6 ]
[ 1402849-66-4 ]