Dimethylformamide → N,N-Dimethyl-4-sulfanylbenzamide

HRID 2120367Notes

Reaction equation

HRID 2120367 reaction equation
[SH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][CH:3]=1.CCOC(C)=O.[CH3:17][N:18](C=O)[CH3:19]>>[CH3:17][N:18]([CH3:19])[C:6]([C:5]1[CH:9]=[CH:10][C:2]([SH:1])=[CH:3][CH:4]=1)=[O:7]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 957384-Mercaptobenzoic acid

Product 1

HCID 13147219N,N-Dimethyl-4-sulfanylbenzamide

Conditions

Temperature
150 °C

Procedure

Di-Phosphorous pentoxide (923 mg) was added to a solution of 4-mercaptobenzoic acid (2000 mg) in DMF (10 ml). The mixture was stirred for sixteen hours at 150° C. under argon. The mixture was allowed to cool then EtOAc (150 ml) was added. The solution was washed with water (100 ml), brine (50 ml) and dried. The volatile material was removed by evaporation and the residue was purified by chromatography on silica gel, eluted with 2.5% MeOH in DCM to give two samples. One sample containing a mixture of thiol and disulphide was purified by chromatography on silica gel, eluted with 1-2.5% MeOH in DCM to give the title compound (760 mg) as a solid. NMR: 2.94 (s, 6H), 5.63 (s, 1H), 7.30 (m, 4H); m/z 180.

Workup

  1. temperatureto cool
  2. washThe solution was washed with water (100 ml), brine (50 ml)
  3. customdried
  4. customThe volatile material was removed by evaporation
  5. customthe residue was purified by chromatography on silica gel
  6. washeluted with 2.5% MeOH in DCM
  7. customto give two samples
  8. additionOne sample containing
  9. customwas purified by chromatography on silica gel
  10. washeluted with 1-2.5% MeOH in DCM

Sources & evidence

ORD record
ord-65f925e312374cb2a1e5a4d6a64286ef
Source dataset
uspto-grants-2004_02
Patent number
US06689909B1

Reaction notes

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