Water → HCID 21537749, compound

HRID 1076590Notes

Reaction equation

HRID 1076590 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH3:18])[C:9]=1[C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:3])[CH3:2].[H-].[Na+].[CH3:21]I.O>CN(C)C=O>[CH3:21][N:4]([C:1](=[O:3])[CH3:2])[C:5]1[S:6][CH:7]=[C:8]([CH3:18])[C:9]=1[C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12426507HCID 12426507, compound

Product 1

HCID 21537749HCID 21537749, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.0 g of 2-acetylamino-3-benzoyl-4-methylthiophene in 20 ml of dimethylformamide is added 0.207 g of 63% sodium hydride. The mixture is stirred at room temperature for 30 minutes. Then 1.64 g of methyl iodide in 4.9 ml of dimethylformaide is added thereto. The mixture is stirred at room temperature for 3 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 to give crystals, which are recrystallized from ether to give N-methyl-2-acetylamino-3-benzoyl-4-methylthiophene as crystals having a melting point of 121.5° - 122.5°C.

Workup

  1. stirringThe mixture is stirred at room temperature for 3 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. customto give crystals, which
  7. customare recrystallized from ether

Sources & evidence

ORD record
ord-813e721f378b47a0879db0ee23dfdbc4
Source dataset
uspto-grants-1976_05
Patent number
US03957783

Reaction notes

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