ChemicalBook CAS DataBase List Benzamide, N,N,4-trimethyl- (9CI)

Benzamide, N,N,4-trimethyl- (9CI) synthesis

6synthesis methods

Product Name:Benzamide, N,N,4-trimethyl- (9CI)
CAS Number:14062-78-3
Molecular formula:C10H13NO
Molecular Weight:163.22

506-59-2 Synthesis

506-59-2
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874-60-2 Synthesis

874-60-2
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14062-78-3
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Yield:14062-78-3 100%

Reaction Conditions:

Stage #1: N,N-dimethylammonium chloridewith triethylamine in N,N-dimethyl-formamide at 0; for 0.0833333 h;
Stage #2: 4-methyl-benzoyl chloride in N,N-dimethyl-formamide at 0; for 0.583333 h;

Steps:

10.R Preparation of N,N-4-trimethylbenzamide

To a stirred solution of N,N-dimethylamine hydrochloride (1.14 g, 14.0 mmol) in DMF (5 mL) at 0 °C was added triethylamine (2.59 mL, 18.6 mmol) and the resulting solution stirred for 5 min. A solution of 4-methylbenzoyl chloride (719 mg, 4.65 mmol) in DMF (5 mL) was then added dropwise over 5 min. The reaction was allowed to stir at 0 °C for a further 30 minutes before warming to rt and partitioning between ethyl acetate (50 mL) and water (50 mL). The phases were separated and the aqueous phase was extracted with ethyl acetate (25mL x 3). The organic layers were then combined, washed (water x 3, brine), dried over Na₂S0₄ and concentrated in vacuo to afford N,N-4-trimethylbenzamide (760 mg, 100%) as a white solid. -NMR (300 MHz; CDC1₃) δ ppm: 2.39 (3H, s), 3.01 (3H, br. s), 3.11 (3H, br. s), 7.19-7.23 (2H, m), 7.31 -7.36 (2H, m).

References:

WO2018/157190,2018,A1 Location in patent:Paragraph 0219

589-18-4 Synthesis