Acetyl chloride → HCID 178474024, compound

HRID 266457Notes

Reaction equation

HRID 266457 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:10](=[CH:11][CH:12]=1)[S:7](=[O:9])(=[O:8])[N:6]([CH:13]([S:20][C:21]1[NH:25][N:24]=[N:23][N:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:5]2=[O:26].[C:27](Cl)(=[O:29])[CH3:28]>C(#N)C>[C:27]([NH:1][C:2]1[CH:3]=[C:4]2[C:10](=[CH:11][CH:12]=1)[S:7](=[O:9])(=[O:8])[N:6]([CH:13]([S:20][C:21]1[NH:25][N:24]=[N:23][N:22]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:5]2=[O:26])(=[O:29])[CH3:28]

Participants

4

Reactant 2

HCID 6367Acetyl chloride2×HCID 178507257HCID 178507257, compound

Product 1

HCID 178474024HCID 178474024, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 0.4 g of 5-amino-2-(1-phenyl-1H-tetrazol-5-ylthiomethyl)saccharin in 25 ml of acetonitrile was treated with 0.08 g (0.001 mol) of acetyl chloride, the mixture was heated under reflux for 30 minutes, treated with an additional drop of acetyl chloride and refluxing continued for another 30 minutes. Evaporation of the mixture to dryness afforded a white foam which was chromatographed on silica gel with 95:5 MDC:ethyl acetate to give 200 mg (43%) of 5-acetylamino-2-(1-phenyl-1H-tetrazol-5-ylthiomethyl)saccharin.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. temperaturerefluxing
  4. customEvaporation of the mixture to dryness
  5. customafforded a white foam which
  6. customwas chromatographed on silica gel with 95:5 MDC

Sources & evidence

ORD record
ord-1209a16a8e904d4292dfe39b82e4c6a1
Source dataset
uspto-grants-1997_07
Patent number
US05650422

Reaction notes

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