Acetone → HCID 20382884, compound

Reaction equation

Cl[CH2:2][C:3]([NH:5][C:6]1[CH:17]=[CH:16][C:9]([C:10]([NH:12][CH2:13][CH2:14][OH:15])=[O:11])=[CH:8][CH:7]=1)=[O:4].[S:18]1C=CC=C1CC([O-])=O.[K+].[CH3:28][C:29](C)=[O:30]>>[C:29]([S:18][CH2:2][C:3]([NH:5][C:6]1[CH:17]=[CH:16][C:9]([C:10]([NH:12][CH2:13][CH2:14][OH:15])=[O:11])=[CH:8][CH:7]=1)=[O:4])(=[O:30])[CH3:28]

Participants

Reactant 3

HCID 180Acetone

HCID 203829064-(2-chloroacetamido)-N-(2-hydroxyethyl)benzamide

HCID 23696799Potassium 2-thienylacetate

Product 1

HCID 20382884HCID 20382884, compoundYield 57%

Procedure

A mixture of 4-(2-chloroacetamido)-N-(2-hydroxyethyl)benzamide (39.3 g., 0.153 mole) and potassium thiolacetate (18.3 g., 0.16 mole) in 650 ml. of acetone is heated at reflux temperature for a period of 2 hr. After standing overnight, the reaction mixture is filtered, the filtercake washed with acetone, slurried with water, filtered and the filtercake washed with water and dried to afford 34.7 g. of crude product. Crystallization of this material from ethyl acetate-methanol affords analytically pure 4-[2-(ACETYLTHIO)ACETAMIDO]-N-(2-HYDROXYETHYL)BENZAMIDE, m.p. 190.0°-192.0° C. (corr.) in 57% yield.