Water → HCID 68089365, compound

HRID 1772007Notes

Reaction equation

HRID 1772007 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12](=[O:14])[CH3:13])=[CH:8][CH:9]=2)[N:4]=[CH:3][CH:2]=1.[H-].[Na+].I[CH3:18].O>C1COCC1>[CH3:18][N:11]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:1]=[CH:2][CH:3]=[N:4]2)[C:12](=[O:14])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 23273816HCID 23273816, compound

Product 1

HCID 68089365HCID 68089365, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(quinoxalin-6-yl)acetamide (8.0 g, 0.043 mol) in THF (120 mL) was added sodium hydride (60% wt in mineral oil, 3.42 g, 0.086 mol). The mixture was stirred at room temperature for 10 min. Then iodomethane (7.28 g, 0.051 mol) was added. The mixture was stirred at room temperature for 2 h. Water (60 mL) was added carefully. The mixture was extracted with EtOAc (3×150 mL). The extracts were dried over sodium sulfate, concentrated to give N-methyl-N-(quinoxalin-6-yl)acetamide as a brown solid (8.04 g, yield 93%). ESI MS: m/z 202.1 [M+H]+.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 h
  2. extractionThe mixture was extracted with EtOAc (3×150 mL)
  3. dry with materialThe extracts were dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3177a101d5ef4114857646bc3a92a376
Source dataset
uspto-grants-2016_02
Patent number
US09249162B2

Reaction notes

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