Dimethylformamide → HCID 19605517, compound

HRID 1603618Notes

Reaction equation

HRID 1603618 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([S:12][C:13]2[CH:14]=[C:15]([NH:19][C:20](=[O:22])[CH3:21])[CH:16]=[CH:17][CH:18]=2)=[CH:8][CH:7]=1)([O-:5])=[O:4].[CH3:23]N(C)C=O>>[CH3:23][N:19]([C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([S:12][C:9]2[CH:10]=[CH:11][C:6]([N+:3]([O-:5])=[O:4])=[CH:7][CH:8]=2)[CH:14]=1)[C:20](=[O:22])[CH3:21]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 19605489HCID 19605489, compound

Product 1

HCID 19605517HCID 19605517, compoundYield 83%

Procedure

0.265 g (0.00657 mol) of NaH (60%) was suspended in 10 ml of dimethylformamide and treated while cooling with ice with a solution of 1.72 g (0.06 mol) of N-[3-(4-nitrophenylsulphanyl)-phenyl]-acetamide in 20 ml of dimethylformamide. After a few minutes the mixture was left to warm to room temperature and stirred for 1 hr. Then, 1.1 ml (0.0179 mol) of Mel were added slowly. The mixture was stirred at room temperature for 18 hrs., the solvent was thereafter removed and the residue was partitioned in water and ethyl acetate. The organic phase was washed with sat. sodium chloride solution, dried over MgSO4 and concentrated. The residue was chromatographed on silica gel with ethyl acetate/hexane 1:1. There were obtained 1.51 g (83%) of N-methyl-N-[3-(4-nitrophenylsulphanyl)-phenyl]-acetamide as yellow crystals; m.p.: 66-68° C.

Workup

  1. additiontreated
  2. waitAfter a few minutes the mixture was left
  3. additionThen, 1.1 ml (0.0179 mol) of Mel were added slowly
  4. stirringThe mixture was stirred at room temperature for 18 hrs
  5. custom, the solvent was thereafter removed
  6. customthe residue was partitioned in water
  7. washThe organic phase was washed with sat. sodium chloride solution
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. customThe residue was chromatographed on silica gel with ethyl acetate/hexane 1:1

Sources & evidence

ORD record
ord-9a426a3a729d4081939cad449103ba4a
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

Loading…