Water → 2-(N-methylacetylamino)-3-benzoyl-4,5,6,7-tetrahydrobenzo[b] thiophene

HRID 1076595Notes

Reaction equation

HRID 1076595 reaction equation
[C:1]([NH:4][C:5]1[S:9][C:8]2[CH2:10][CH2:11][CH2:12][CH2:13][C:7]=2[C:6]=1[C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:3])[CH3:2].[H-].[Na+].[CH3:24]I.O>CN(C)C=O>[CH3:24][CH2:2][C:1]([NH:4][C:5]1[S:9][C:8]2[CH2:10][CH2:11][CH2:12][CH2:13][C:7]=2[C:6]=1[C:14](=[O:21])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 902348AK-660/12300001

Product 1

HCID 124265102-(N-methylacetylamino)-3-benzoyl-4,5,6,7-tetrahydrobenzo[b] thiophene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 5.0 g of 2-acetylamino-3-benzoyl-4,5,6,7-tetrahydrobenzo[b ]thiophene in 60 ml of dimethylformamide is added 0.9 g of 63% sodium hydride. The mixture is stirred at room temperature for 30 minutes. Then 71.3 g of methyl iodide in 20 ml of dimethylformamide 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 2-(N-methylacetylamino)-3-benzoyl-4,5,6,7-tetrahydrobenzo[b] thiophene as an oil. This layer chromatography (Kiesel gel) shows the Rf value of 0.44 using a mixture of ethyl acetate and chloroform (1 : 1 V/V).

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

Sources & evidence

ORD record
ord-00d009d7c0bf458c922f20ce76d8e485
Source dataset
uspto-grants-1976_05
Patent number
US03957783

Reaction notes

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