Cyclohexane → N'-(4'-tert-butyl-2,5-dimethylbiphenyl-4-yl)-N-ethyl-N-methylimidoformamide

HRID 1673193Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[C:15]([CH3:17])[C:14]([NH2:18])=[CH:13][C:12]=2[CH3:19])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CO[CH:22](OC)[N:23]([CH3:26])[CH2:24][CH3:25].C1CCCCC1.C(OCC)(=O)C>CO>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:16]=[C:15]([CH3:17])[C:14]([N:18]=[CH:22][N:23]([CH2:24][CH3:25])[CH3:26])=[CH:13][C:12]=2[CH3:19])=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 45 °C

Procedure

To a mixture of 2.1 g (6.3 mmol) of 4′-tert-butyl-2,5-dimethylbiphenyl-4-amine in 2.5 ml methanol a solution of 8.8 mmol of N-(dimethoxymethyl)-N-methylethanamine (60% in methanol) was added. The reaction mixture was stirred for 24 hrs at 45° C. The reaction mixture was concentrated in vacuo. Column chromatographic (gradient: cyclohexane->ethyl acetate) yielded 0.96 g (3.0 mmol) 47% of N′-(4′-tert-butyl-2,5-dimethylbiphenyl-4-yl)-N-ethyl-N-methylimidoformamide; log P (pH 2.3)=2.67.

Workup

additionwas added
concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-545e92ada8484eeabc91f9a66c5947e3
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07999137B2

Reaction notes

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