Ethyl Bromide → HCID 12803383, compound

HRID 1758338Notes

Reaction equation

HRID 1758338 reaction equation
[C:1]1([N:7]2[C:11]([S:12][CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:10][N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:27](Br)[CH3:28]>CN(C)C=O>[C:1]1([N:7]2[C:11]([S:12][CH2:13][CH2:14][CH2:15][N:16]([CH2:27][CH3:28])[C:17](=[O:24])[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[N:10][N:9]=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 12803382HCID 12803382, compound

Product 1

HCID 12803383HCID 12803383, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Phenyl-5-[3-(N-benzoylamino)propylthio]-1,2,3,4-tetrazole (1.7 g) is dissolved in dimethylformamide (30 ml). To the mixture is added with stirring 50% oily sodium hydride (0.3 g) at room temperature. After foaming is finished, the mixture is stirred at 60°-70° C. for one hour. After cooling until room temperature, ethyl bromide (0.8 g) is added dropwise to the resulting mixture, and thereafter, the mixture is stirred at 60°-70° C. for 8 hours. After dimethylformamide is distilled off, the residue is purified by column chromatography (Wakogel C-200), followed by eluting with chloroform to give 1-phenyl-5[3-(N-ethyl-N-benzoylamino)propylthio]-1,2,3,4-tetrazole (1.2 g), as a colorless liquid, nD24 =1.5898.

Workup

  1. additionTo the mixture is added
  2. stirringthe mixture is stirred at 60°-70° C. for 8 hours
  3. distillationAfter dimethylformamide is distilled off
  4. customthe residue is purified by column chromatography (Wakogel C-200)
  5. washby eluting with chloroform

Sources & evidence

ORD record
ord-f75d9ca488a34c31bb6060ef58f42b7c
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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