Dimethylformamide → (E)-1-(4-tert-butylphenyl)-1-cyclopropyl-N-[(2-methyl-3-phenylphenyl)methoxy]methanimine

HRID 1388945Notes

Reaction equation

HRID 1388945 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8](/[C:11](/[CH:14]2[CH2:16][CH2:15]2)=[N:12]/[OH:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[CH2:20][C:21]1[C:22]([CH3:33])=[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=[CH:25][CH:26]=1.CN(C)C=O>C1(C)C=CC=CC=1>[CH3:33][C:22]1[C:21]([CH2:20][O:13]/[N:12]=[C:11](/[C:8]2[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][CH:9]=2)\[CH:14]2[CH2:16][CH2:15]2)=[CH:26][CH:25]=[CH:24][C:23]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 13282518(NE)-N-[(4-tert-butylphenyl)-cyclopropylmethylidene]hydroxylamineHCID 132825193-(Chloromethyl)-2-methyl-1,1'-biphenyl

Product 1

HCID 13282542(E)-1-(4-tert-butylphenyl)-1-cyclopropyl-N-[(2-methyl-3-phenylphenyl)methoxy]methanimine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a manner similar to Example 2, the reaction of 0.75 g (0.0034 mole) of (E)-(4-t-butylphenyl)(cyclopropyl)methanone oxime with 0.2 g (0.008 mole) of sodium hydride and 0.74 g (0.0034 mole) of 3-chloromethyl-2-methyl[1,1'-biphenyl] in 25 ml of a 20% solution of N,N-dimethylformamide in toluene produced (E)-(4-t-butylphenyl)(cyclopropyl)methanone O-[(2-methyl[1,1'-biphenyl]-3-yl)methyl]oxime as an oil.

Sources & evidence

ORD record
ord-6e1d7188291547ceaa947026491a5f39
Source dataset
uspto-grants-1984_02
Patent number
US04434182

Reaction notes

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