Methyl iodide → N-(3-chloro-4-fluorophenyl)N-methylformamide

HRID 127821Notes

Reaction equation

HRID 127821 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([NH:11][CH:12]=[O:13])[CH:7]=[CH:8][C:9]=1[F:10].[CH3:14]I>O1CCCC1>[Cl:3][C:4]1[CH:5]=[C:6]([N:11]([CH3:14])[CH:12]=[O:13])[CH:7]=[CH:8][C:9]=1[F:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 237238N-(3-chloro-4-fluorophenyl)formamide

Product 1

HCID 12876631N-(3-chloro-4-fluorophenyl)N-methylformamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

17.5 g of sodium hydride (57% in mineral oil) was added, in portions, to a stirred solution of 55.5 g of 1A and 71 g of methyl iodide in 250 ml of tetrahydrofuran at room temperature. The resulting mixture was stirred and refluxed for 2 hours, poured into ice water and filtered. The solid was washed with water, dried and recrystallized from hexane to give N-(3-chloro-4-fluorophenyl)N-methylformamide (5A), as a white crystalline solid, mp: 47°-48° C.

Workup

  1. temperaturerefluxed for 2 hours
  2. filtrationfiltered
  3. washThe solid was washed with water
  4. customdried
  5. customrecrystallized from hexane

Sources & evidence

ORD record
ord-8a5b7edf9b084ce7bc2baddfb4b9a584
Source dataset
uspto-grants-1981_03
Patent number
US04257805

Reaction notes

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