Dimethylformamide → (E)-1-(4-chlorophenyl)-1-cyclopropyl-N-[(2,4-difluoro-3-phenylphenyl)methoxy]methanimine

HRID 1388944Notes

Reaction equation

HRID 1388944 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[CH:11]2[CH2:13][CH2:12]2)=[N:9]/[OH:10])=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:17][C:18]1[C:19]([F:31])=[C:20]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:21]([F:24])=[CH:22][CH:23]=1.CN(C)C=O>C1(C)C=CC=CC=1>[F:31][C:19]1[C:18]([CH2:17][O:10]/[N:9]=[C:8](/[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)\[CH:11]2[CH2:12][CH2:13]2)=[CH:23][CH:22]=[C:21]([F:24])[C:20]=1[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 6051044(E)-(4-chlorophenyl)(cyclopropyl)methanone oximeHCID 204691843-Chloromethyl-2,6-difluoro[1,1'-biphenyl]

Product 1

HCID 88714665(E)-1-(4-chlorophenyl)-1-cyclopropyl-N-[(2,4-difluoro-3-phenylphenyl)methoxy]methanimine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a manner similar to Example 2, the reaction of 0.59 g (0.003 mole) of (E)-(4-chlorophenyl)(cyclopropyl)methanone oxime with 0.072 g (0.003 mole) of sodium hydride and 0.72 g (0.003 mole) of 3-chloromethyl-2,6-difluoro[1,1'-biphenyl] in 25 ml of a 20% solution of N,N-dimethylformamide in toluene produced (E)-(4-chlorophenyl)(cyclopropyl)methanone O-[(2,6-difluoro[1,1'-biphenyl]-3-yl)methyl]oxime as an oil.

Sources & evidence

ORD record
ord-2344cd1ce09c4675a81298a2ecec50d2
Source dataset
uspto-grants-1984_02
Patent number
US04434182

Reaction notes

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