Dimethylformamide → HCID 67271990, compound

HRID 250877Notes

Reaction equation

HRID 250877 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:13])[CH3:12])[CH:7]=[CH:8][CH:9]=1.[CH2:14](I)[CH3:15].CN(C)C=O>O1CCCC1>[Br:3][C:4]1[CH:5]=[C:6]([N:10]([CH2:14][CH3:15])[C:11](=[O:13])[CH3:12])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 12123N-(3-Bromophenyl)acetamideHCID 24758Sodium hydride

Product 1

HCID 67271990HCID 67271990, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

820 mg (20.5 mmol, 1.1 eq) of 60% sodium hydride are added to a solution of 4.0 g (18.7 mmol, 1 eq) of N-(3-bromophenyl)acetamide and 1.80 mL (22.4 mmol, 1.2 eq) of ethyl iodide in 15 ml of tetrahydrofuran in the presence of 1.5 ml of dimethylformamide. The reaction medium is stirred at room temperature for 12 hours and then hydrolyzed with water and extracted with ethyl acetate. The organic phases are combined, washed with sodium chloride solution and dried over sodium sulfate. The solvents are evaporated off and the N-(3-bromophenyl)-N-ethylacetamide obtained in oil form is used in the following reaction without further purification.

Workup

  1. extractionhydrolyzed with water and extracted with ethyl acetate
  2. washwashed with sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customThe solvents are evaporated off

Sources & evidence

ORD record
ord-0f32b78ee59147788d54de37ff1276dd
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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