Water → HCID 21537737, compound

HRID 1076611Notes

Reaction equation

HRID 1076611 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH3:19])[C:9]=1[C:10](=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:17])(=[O:3])[CH3:2].[H-].[Na+].[CH3:22]I.O>CN(C)C=O>[CH3:22][CH2:2][C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH3:19])[C:9]=1[C:10](=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:17])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21537730HCID 21537730, compound

Product 1

HCID 21537737HCID 21537737, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 40.0 g of 2-acetylamino-3-(o-chlorobenzoyl)-4-methylthiophene in 800 ml of dimethylformamide is added 7.74 g of 63 % sodium hydride. The mixture is stirred at room temperature for 30 minutes. Then 61.34 g of methyl iodide in 184 ml of dimethylformamide is added thereto. The mixture is stirred at room temperature for 2 hours, 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 2-(N-methylacetylamino)-3-(o-chlorobenzoyl)-4-methylthiophene as an oil.

Workup

  1. stirringThe mixture is stirred at room temperature for 2 hours
  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

Sources & evidence

ORD record
ord-393b181abd654a7c98c61536ae9a75b4
Source dataset
uspto-grants-1976_05
Patent number
US03957783

Reaction notes

Loading…