Ammonia → 2-sulfanylbenzamide

HRID 1033707Notes

Reaction equation

HRID 1033707 reaction equation
[S:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](=O)[O:3]C1=O.[NH3:13]>>[C:4]([NH2:13])(=[O:3])[C:5]1[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=1)[SH:1]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 19024279HCID 19024279, compound

Product 1

HCID 3506572-sulfanylbenzamideYield 99%

Procedure

An amount of 1.94 g of the compound of Example 1 was dissolved in 50 ml of ammonia saturated methanol, the solution was stirred at room temperature for 20 minutes, the methanol was evaporated, and an aqueous citric acid solution added followed by an extraction with ethyl acetate. After washing with aqueous sodium chloride, the mixture was dried over anhydrous magnesium sulfate, the ethyl acetate solution was concentrated, and the residue developed with methylene chloridemethanol (97:3) by silica gel column chromatography to obtain 1.63 g of the desired compound (yield 99.0%).

Workup

  1. customthe methanol was evaporated
  2. additionan aqueous citric acid solution added
  3. extractionfollowed by an extraction with ethyl acetate
  4. washAfter washing with aqueous sodium chloride
  5. dry with materialthe mixture was dried over anhydrous magnesium sulfate
  6. concentrationthe ethyl acetate solution was concentrated

Sources & evidence

ORD record
ord-ae26edd51f554619a986fff65583cc99
Source dataset
uspto-grants-1994_05
Patent number
US05312625

Reaction notes

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