Sodium Chloride → (E)-N-(2-(fluoromethylene)-4-(p-fluorophenyl)butyl)-N-formyl formamide

HRID 1449855Notes

Reaction equation

[CH:1]([N-:3][CH:4]=[O:5])=[O:2].[Na+].C(#N)C.Cl[CH2:11]/[C:12](=[CH:22]/[F:23])/[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1.[Cl-].[Na+]>C1(C)C=CC=CC=1.O.CN(C)C=O>[F:23]/[CH:22]=[C:12](\[CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=1)/[CH2:11][N:3]([CH:4]=[O:5])[CH:1]=[O:2]

Participants

Conditions

Temperature: 80 °C

Procedure

Combine sodium diformylamide (70 lb) and acetonitrile (903 lb). With agitation, add N,N-dimethylformamide (119 lb). Add a solution of (E)-1-chloro-2-(fluoromethylene)-4-(p-fluorophenyl)butane (126 lb) in toluene. Warm to 80° C. After 6 hours, add a 10% by weight solution of sodium chloride in water (1168 lb). Agitate for 15 minutes, separate the layers. Remove the organic layer to give the title compound as a solution in acetonitrile/N,N-dimethylformamide.

Workup

customseparate the layers
customRemove the organic layer

Sources & evidence

ORD record: ord-73fdb5f652bb47e49c7344d800ba6cbc
Source dataset: uspto-grants-1997_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05599986

Reaction notes

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