Water → HCID 178475125, compound

HRID 1076607Notes

Reaction equation

HRID 1076607 reaction equation
C(N[C:5]1[S:6][CH:7]=[CH:8][C:9]=1[C:10](=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17])(=O)C.[H-].[Na+].[CH3:21]I.O.[CH3:24][N:25](C)[CH:26]=[O:27]>>[CH3:24][N:25]([C:26](=[O:27])[CH3:21])[SH:6]1[CH:7]=[CH:8][C:9]([C:10](=[O:18])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])=[CH:5]1

Participants

6

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12202377HCID 12202377, compound

Product 1

HCID 178475125HCID 178475125, compound

Procedure

To a solution of 1.0 g of 2-acetylamino-3-(o-fluorobenzoyl)thiophene in 10 ml of dimethylformamide is added 0.220 g of 63 % sodium hydride. The mixture is stirred at room temperature for 30 minutes. Then 1.0 g of methyl iodide in 1 ml of dimethylformamide is added thereto. The mixture is stirred at room temperature overnight, then poured into water, and extracted with benzene. The benzene extracts are washed with water, dried over sodium sulfate, and the solvent is removed under reduced pressure. The residual oil is chromatographed on silica gel, using chloroform as an eluent to give crystals, which are recrystallized from ether to give N-methyl-1-acetylamino-3-(o-fluorobenzoyl)thiophene as crystals having a melting point of 94° - 95°C.

Workup

  1. stirringThe mixture is stirred at room temperature overnight
  2. extractionextracted with benzene
  3. washThe benzene extracts are washed with water
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is removed under reduced pressure
  6. customThe residual oil is chromatographed on silica gel
  7. customto give crystals, which
  8. customare recrystallized from ether

Sources & evidence

ORD record
ord-19260b73794149ddb99db7a0cb109ad5
Source dataset
uspto-grants-1976_05
Patent number
US03957783

Reaction notes

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