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

HRID 236894Notes

Reaction equation

HRID 236894 reaction equation
[CH3:1][NH:2][C:3]1[S:4][C:5]([CH3:8])=[N:6][N:7]=1.[C:9](Cl)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>N1C=CC=CC=1>[CH3:1][N:2]([C:3]1[S:4][C:5]([CH3:8])=[N:6][N:7]=1)[C:9](=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 3161286N,5-Dimethyl-1,3,4-thiadiazol-2-amine

Product 1

HCID 12679001N-Methyl-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-(N-Methyl-amino)-5-methyl-1,3,4-thiadiazole (6 g, 0.046 mole) in pyridine (190 ml) was refluxed for 6 hours with benzoyl chloride (9.7 g, 0.069 mole) and the pyridine then evaporated off under reduced pressure. The residue was treated with water, made alkaline with sodium hydroxide solution and extracted with chloroform. The chloroform was washed with a saturated solution of sodium bicarbonate and a saturated solution of sodium chloride, dried, filtered and evaporated to yield title product which was recrystallised from ethanol.

Workup

  1. customthe pyridine then evaporated off under reduced pressure
  2. additionThe residue was treated with water
  3. extractionextracted with chloroform
  4. washThe chloroform was washed with a saturated solution of sodium bicarbonate
  5. dry with materiala saturated solution of sodium chloride, dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-0f7d663c8805411e8a49469943e8724a
Source dataset
uspto-grants-1979_06
Patent number
US04158659

Reaction notes

Loading…