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

HRID 236899Notes

Reaction equation

HRID 236899 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

5

Reactant 4

HCID 241BenzeneHCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 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.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 20 hours
  3. customThe solution was then evaporated to dryness
  4. additionthe residue treated with ether
  5. filtrationfiltered
  6. washThe solution was washed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customthe residue recrystallised from petrol ether (40°-60° C.)

Sources & evidence

ORD record
ord-dc0c8aa858864768b932f674958f8885
Source dataset
uspto-grants-1979_06
Patent number
US04158659

Reaction notes

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