3',4'-DICHLOROPIVALANILIDE synthesis

Yield:7160-22-7 195 g (86%)

Reaction Conditions:

with aq NaOH in methanol;water;

Steps:

2 Preparation of N-(3,4-dichlorophenyl)2,2-dimethyl-propionamide.

Preparation of N-(3,4-dichlorophenyl)2,2-dimethyl-propionamide. 3,4-dichloroaniline (150 g) in TBME (1L) was cooled to 10-15° C. 30% aq NaOH (141 g, 1.14 equiv) was added, and the solution stirred vigorously via overhead mechanical stirrer., Trimethylacetyl chloride ("PivCl", 126 mL) was added at such a rate as to keep the internal temperature below 30° C. During this addition, the solution mixture becomes thick with white solid product. When the addition was complete (10-15 min), the mixture was heated to 30-35° C. for 1 hr, and then allowed to cool. The reaction mixture was held at -5° C. (overnight), and then filtered, rinsing first with 90:10 water/MeOH (600 mL) and then water (900 mL). Drying under vacuum yielded 195 g (86%) product, as off-white crystals. LCMS m/z 246(M-H)⁺.

References:

US2003/216375,2003,A1