Methyl iodide → N-(3-chloro-4-fluorophenyl)N-methylformamide
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
Product 1
Reagents, catalysts & solvents 1
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
- temperaturerefluxed for 2 hours
- filtrationfiltered
- washThe solid was washed with water
- customdried
- customrecrystallized from hexane
Sources & evidence
- ORD record
- ord-8a5b7edf9b084ce7bc2baddfb4b9a584
- Source dataset
- uspto-grants-1981_03
- Patent number
- US04257805
Reaction notes
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