Water → 3-Bromo-N-cyclopropyl-4,N-dimethyl-benzamide

HRID 2377418Notes

Reaction equation

HRID 2377418 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[CH3:14])[C:5]([NH:7][CH:8]1[CH2:10][CH2:9]1)=[O:6].[H-].[Na+].[CH3:17]I.O>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[CH3:14])[C:5]([N:7]([CH:8]1[CH2:9][CH2:10]1)[CH3:17])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 211071523-bromo-N-cyclopropyl-4-methylbenzamide2×

Product 1

HCID 211071533-Bromo-N-cyclopropyl-4,N-dimethyl-benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred, cooled (ice bath) solution of 3-bromo-N-cyclopropyl-4-methyl-benzamide (Intermediate 95, 6 g, 23.25 mmol) in anhydrous tetrahydrofuran (100 mL) under argon was treated with small portions of sodium hydride (1.6 g, 40 mmol, 60% dispersion in mineral oil). The reaction mixture was allowed to warm to ambient temperature and after 1 h, methyl iodide (3.11 mL, 50 mmol) was added and the reaction mixture was refluxed for 5 h. It was cooled to ambient temperature, poured into cold water and extracted with diethyl ether (×2). The combined organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title product as a dirty brown solid that was used as such for the next step (6.3 g, 100%).

Workup

  1. temperaturethe reaction mixture was refluxed for 5 h
  2. temperatureIt was cooled to ambient temperature
  3. extractionextracted with diethyl ether (×2)
  4. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-8035f846b33d419bb7946064d97c5cb3
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

Loading…