Dimethylformamide → (E)-1-(4-chlorophenyl)-1-cyclopropyl-N-[(2,4,6-trifluoro-3-phenylphenyl)methoxy]methanimine

HRID 1388943Notes

Reaction equation

HRID 1388943 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:32])=[C:20]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:21]([F:25])=[CH:22][C:23]=1[F:24].CN(C)C=O>C1(C)C=CC=CC=1>[F:32][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)=[C:23]([F:24])[CH:22]=[C:21]([F:25])[C:20]=1[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 6051044(E)-(4-chlorophenyl)(cyclopropyl)methanone oximeHCID 132825203-Chloromethyl-2,4,6-trifluoro[1,1'-biphenyl]

Product 1

HCID 13282522(E)-1-(4-chlorophenyl)-1-cyclopropyl-N-[(2,4,6-trifluoro-3-phenylphenyl)methoxy]methanimineYield 40.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a manner similar to Example 6 of U.S. Pat. No. 4,079,149, 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 0.77 g (0.003 mole) of 3-chloromethyl-2,4,6-trifluoro[1,1'-biphenyl] in 25 ml of a 20% solution of N,N-dimethylformamide in toluene produced 0.5 g of (E)-(4-chlorophenyl)(cyclopropyl)methanone O-[(2,4,6-trifluoro[1,1'-biphenyl]-3-yl)methyl]oxime as an oil.

Sources & evidence

ORD record
ord-b3b6ac407bf044eb9679b9e6ea492a34
Source dataset
uspto-grants-1984_02
Patent number
US04434182

Reaction notes

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