p-Anisoyl chloride → HCID 20509822, compound

HRID 1758340Notes

Reaction equation

HRID 1758340 reaction equation
[CH3:1][N:2]1[C:6]([S:7][CH2:8][CH2:9][CH2:10][NH2:11])=[N:5][N:4]=[N:3]1.C(=O)([O-])[O-].[K+].[K+].[CH3:18][O:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1>CC(C)=O.O>[CH3:1][N:2]1[C:6]([S:7][CH2:8][CH2:9][CH2:10][NH:11][C:24](=[O:25])[C:23]2[CH:27]=[CH:28][C:20]([O:19][CH3:18])=[CH:21][CH:22]=2)=[N:5][N:4]=[N:3]1

Participants

6

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 11430Potassium CarbonateHCID 12803379HCID 12803379, compound

Product 1

HCID 20509822HCID 20509822, compoundYield 43.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

1-Methyl-5-(3-aminopropylthio)-1,2,3,4-tetrazole (0.9 g) is dissolved in a mixture of acetone (50 ml) and water (10 ml). To the mixture is added potassium carbonate (0.7 g) and thereto is added dropwise with stirring 4-methoxybenzoylchloride (1.1 g) under ice-cooling. Stirring is continued for 2 hours under ice-cooling. After acetone is distilled off, water is added to the resulting residue and the mixture is extracted with chloroform. The chloroform solution is washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride and dried over sodium sulfate. Chloroform is distilled off and then the residue is purified by column chloratography (Wakogel C-200), followed by eluting with chloroform to give 1-methyl-5-{3-[N-(4-methoxybenzoyl)amino]propylthio}-1,2,3,4-tetrazole (0.7 g), colorless needles (ethyl acetate-ethanol), m.p. 118°-122° C.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. distillationAfter acetone is distilled off
  4. additionwater is added to the resulting residue
  5. extractionthe mixture is extracted with chloroform
  6. washThe chloroform solution is washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  7. dry with materialdried over sodium sulfate
  8. distillationChloroform is distilled off
  9. customthe residue is purified by column chloratography (Wakogel C-200)
  10. washby eluting with chloroform

Sources & evidence

ORD record
ord-04edc4d313aa4ec8bce009d229e3fad1
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

Loading…