Benzene → N-Butyl-N-(5-methyl-1,3,4-thiadiazol-2-yl)cyclopropanecarboxamide

Reaction equation

C[C:2]1[S:6][C:5]([CH2:7]CCCN)=[N:4][N:3]=1.C([N:14]([CH2:17][CH3:18])CC)C.[CH:19]1([C:22](Cl)=[O:23])[CH2:21][CH2:20]1.[CH:25]1C=CC=C[CH:26]=1>>[CH2:17]([N:14]([C:2]1[S:6][C:5]([CH3:7])=[N:4][N:3]=1)[C:22]([CH:19]1[CH2:21][CH2:20]1)=[O:23])[CH2:18][CH2:25][CH3:26]

Participants

Reactant 4

HCID 241Benzene

HCID 8471Triethylamine

HCID 77637Cyclopropanecarbonyl chloride

HCID 70601298HCID 70601298, compound

Product 1

HCID 21315319N-Butyl-N-(5-methyl-1,3,4-thiadiazol-2-yl)cyclopropanecarboxamide

Procedure

N-(5-methyl-1,3,4-thiadiazol-2-yl)butylamine (1.7 g, 0.01 mole) in benzene (20 ml) was treated with triethylamine (1.53 ml) and cyclopropane carboxylic acid chloride (1.15 g). The reaction mixture was heated to reflux for 20 hours. The solution was then evaporated to dryness and the residue treated with ether and filtered. The solution was washed with water, dried and charcoaled, filtered and evaporated and the residue recrystallised from petrol ether (40°-60° C.) to give N-butyl-N-(5-methyl-1,3,4-thiadiazol-2-yl)cyclopropane carboxamide as a white crystalline solid. m.p. 82°-84° C.