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ChemicalBook CAS DataBase List 2-Chloro-N-(2,6-dimethylphenyl)acetamide
1131-01-7

2-Chloro-N-(2,6-dimethylphenyl)acetamide synthesis

9synthesis methods
Chloroiodomethane

593-71-5

2,6-Dimethylphenyl isocyanate

28556-81-2

2-Chloro-N-(2,6-dimethylphenyl)acetamide

1131-01-7

General method: Chloroiodomethane (1.5 eq.) is slowly added to a solution of 2,6-dimethylphenyl isocyanate (1.0 eq.) in anhydrous ether (1 M concentration) at -78 °C. After 2 minutes of reaction, a 1.5 M solution of methyl lithium-lithium bromide (1.25 equiv.) ether was added dropwise over 5 minutes. Maintaining this temperature, the reaction mixture was stirred for the indicated time (see Table 1 and Scheme 2 for specific times). Upon completion of the reaction, aqueous ammonium chloride solution (2 mL/mmol substrate) was added, the cooling bath was removed, and stirring was continued until the mixture was brought to room temperature. Subsequently, the reaction mixture was extracted with ether (2 x 5 mL) and the organic phase was washed sequentially with water (5 mL) and brine (10 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give pure 2,6-dimethylchloroacetanilide.

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Yield:1131-01-7 89%

Steps:

289.A 2-chloro-N-(2,6-dimethylphenyl)acetamide
EXAMPLE 289A 2-chloro-N-(2,6-dimethylphenyl)acetamide The procedure described in Example 22A was followed, substituting 2,6-dimethylphenylamine for 3,4,5-trimethoxyaniline to provide the title compound (7.21 g, 89%) 1H NMR (300 MHz, CDCl3) δ 2.25 (s, 6H), 4.26 (s, 2H), 6.65 (t, J=7.46 Hz, 1H, 6.95 (d, J=7.46 Hz, 2H), 7.84 (s, 3H); MS (ESI) m/e 198 (M+H)+.

References:

Bhatia, Pramila A.;Daanen, Jerome F.;Hakeem, Ahmed A.;Kolasa, Teodozyj;Matulenko, Mark A.;Mortell, Kathleen H.;Patel, Meena V.;Stewart, Andrew O.;Wang, Xueqing;Xia, Zhiren;Zhang, Henry Q. US2004/29887, 2004, A1

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