Sodium hydride → 2-chloro-N-(2-methylthiazol-4-yl)methyl-N-(2,6-dimethylphenyl)acetamide

HRID 27336

Reaction equation

HRID 27336 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13])=[O:4].[CH3:14][C:15]1[S:16][CH:17]=[C:18]([CH2:20]Cl)[N:19]=1.[H-].[Na+]>CN(C)C=O>[Cl:1][CH2:2][C:3]([N:5]([CH2:20][C:18]1[N:19]=[C:15]([CH3:14])[S:16][CH:17]=1)[C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13])=[O:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 707982-Chloro-N-(2,6-dimethylphenyl)acetamideHCID 7363414-(Chloromethyl)-2-methyl-1,3-thiazole

Product 1

HCID 130376012-chloro-N-(2-methylthiazol-4-yl)methyl-N-(2,6-dimethylphenyl)acetamideYield 18%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5.33 g N-chloroacetyl-2,6-dimethylaniline and 4 g 2-methyl-4-chloromethylthiazole (prepared in Example 4A above) in dry dimethylformamide was treated with 1.56 g sodium hydride as in Example 3 above. After workup, the solid product was purified by high-pressure liquid chromatography to yield 1.5 g pure product, m.p. 62°-64° C. This product is shown as Compound 3 in Table I. C15H17ClN2OS: calc., %C 58.35, %H 5.51, %N 9.08; found, %C 59.23, %H 5.79, %N 9.28.

Workup

  1. customAfter workup, the solid product was purified by high-pressure liquid chromatography

Sources & evidence

ORD record
ord-1b9a025333954829949511d480f9dfcc
Source dataset
uspto-grants-1980_09
Patent number
US04221584

Linked notes

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