Methyl iodide → HCID 20378192, compound

HRID 1391207Notes

Reaction equation

HRID 1391207 reaction equation
[H-].[Na+].[C:3]([C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[NH:18][CH:19]=[O:20])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H][H].[CH3:23]I>CN(C)C=O.O>[CH3:23][N:18]([C:12]1[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:11]=1[C:3](=[O:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH:19]=[O:20]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 82576N-(2-Benzoyl-4-chlorophenyl)formamideHCID 178418361HCID 178418361, compound

Product 1

HCID 20378192HCID 20378192, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.8 mole, 38.4 g of 50% in mineral oil) was added to a solution of 197.4 g (0.76 mole) of N-(2-benzoyl-4-chlorophenyl)formamide in 800 ml dimethylformamide. When the evolution of hydrogen ceased, 184 g of methyl iodide was added dropwise at such a rate that the temperature of the reaction mixture slowly rose to 70°. The reaction mixture was stirred for 90 min., and then poured into 2 l. of water. The aqueous mixture was extracted four times with 300 ml portions of methylene chloride, and the combined extracts were washed with water, dried (MgSO4) and evaporated to dryness under reduced pressure. The residue was recrystallized from methanol to give 145.4 g (70% yield) of the N-methylformamide as colorless crystals: mp 93.5°-94.5°; 1H nmr (CDCl3) showed two methyl peaks at δ 2.94 and 3.23 ppm (ratio 70:30).

Workup

  1. customslowly rose to 70°
  2. additionpoured into 2 l
  3. extractionThe aqueous mixture was extracted four times with 300 ml portions of methylene chloride
  4. washthe combined extracts were washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated to dryness under reduced pressure
  7. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-46e8c990bfda40438b617c8c1619e963
Source dataset
uspto-grants-1979_02
Patent number
US04141895

Reaction notes

Loading…