Benzoyl chloride → N-(5-Methyl-1,3,4-thiadiazol-2-yl)-N-(propan-2-yl)benzamide

HRID 261797Notes

Reaction equation

HRID 261797 reaction equation
[CH3:1][C:2]1[S:6][C:5]([NH:7][CH:8]([CH3:10])[CH3:9])=[N:4][N:3]=1.[C:11](Cl)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>N1C=CC=CC=1>[CH3:9][CH:8]([N:7]([C:5]1[S:6][C:2]([CH3:1])=[N:3][N:4]=1)[C:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:10]

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 5446705-Methyl-N-(propan-2-yl)-1,3,4-thiadiazol-2-amine

Product 1

HCID 21315328N-(5-Methyl-1,3,4-thiadiazol-2-yl)-N-(propan-2-yl)benzamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N-(5-methyl-1,3,4-thiadiazol-2-yl)-1-methylethylamine (5 g, 0.032 mole) in pyridine (100 ml) was treated with benzoyl chloride (4.1 ml). The reaction mixture was stirred and heated to reflux for 51/2 hours. The pyridine was removed under reduced pressure and the residue treated with water and extracted with ether (×3). The ethereal solution was dried, filtered and evaporated to dryness and the residue recrystallised from ether/petrol ether (40°-60° C.) to give the title compound as a pale yellow crystalline solid m.p. 82.5°-83.5° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 51/2 hours
  3. customThe pyridine was removed under reduced pressure
  4. additionthe residue treated with water
  5. extractionextracted with ether (×3)
  6. customThe ethereal solution was dried
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customthe residue recrystallised from ether/petrol ether (40°-60° C.)

Sources & evidence

ORD record
ord-e977dbbd8ab9440aadb77a5a858a5ba8
Source dataset
uspto-grants-1979_05
Patent number
US04152442

Reaction notes

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