Dimethyl Sulfoxide → 4-Bromophenylthiomethanesulfonamide

HRID 1194003Notes

Reaction equation

HRID 1194003 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7](S)=[CH:6][CH:5]=1.Br[CH2:12][S:13]([NH2:16])(=O)=[O:14].C(OCC)(=O)C.C[S:24](C)=O>>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:12][S:13]([NH2:16])(=[S:24])=[O:14])=[CH:6][CH:5]=1

Participants

6

Reactant 5

HCID 679Dimethyl Sulfoxide2×HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 660494-BromothiophenolHCID 12268467Bromomethanesulfonamide

Product 1

HCID 679302784-BromophenylthiomethanesulfonamideYield 81.4%

Conditions

Temperature
80 °C

Procedure

A suspension of 1.4 g of a 60% sodium hydride/oil dispersion was prepared in 10 ml of dry DMSO, under an atmosphere of nitrogen. 4-Bromothiophenol (6.5 g) was dissolved in 11 ml of dry DMSO and added slowly to the above suspension. When frothing had subsided 6.0 g of bromomethanesulfonamide was added and the reaction mixture was heated to 80° C. for 2 hours. The reaction mixture was cooled to room temperature and poured into 150 ml of ethyl acetate, filtered from a solid and extracted with brine. The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum. The resultant residue was recrystallized from toluene to yield 7.9 g (81.4%) of product.

Workup

  1. additionadded slowly to the above suspension
  2. additionwas added
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationfiltered from a solid
  5. extractionextracted with brine
  6. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe resultant residue was recrystallized from toluene

Sources & evidence

ORD record
ord-15ca3e9b2397479bbff1bee21550c35e
Source dataset
uspto-grants-1989_03
Patent number
US04812463

Reaction notes

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