Diphenylamine → Urea, N-butyl-N',N'-diphenyl-N-(phenylmethyl)-

HRID 2418687Notes

Reaction equation

[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(N(C)C)=O.[CH2:20]([N:27]([CH2:31][CH2:32][CH2:33][CH3:34])[C:28](Cl)=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[H-].[Na+]>O>[CH2:20]([N:27]([CH2:31][CH2:32][CH2:33][CH3:34])[C:28]([N:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 3.89 g. of diphenylamine in 25 ml. of dimethylacetamide is added during one hour to a stirred mixture of 5.19 g. of N-benzyl-N-(n-butyl)carbamyl chloride, 0.685 g. of sodium hydride, and 65 ml. of dimethylacetamide under a nitrogen atmosphere at 45°-50° C. The mixture is stirred for 2 hours at 50° C. and then poured into water. The mixture is extracted with methylene chloride and the extract is evaporated. The residue is purified by chromatography using silica gel as the adsorbant and acetone-hexane as the eluent. After evaporation of the eluent, the residue is evaporatively distilled at 165° C. under reduced pressure (150 microns) to yield 1-benzyl-1-(n-butyl)-3,3-diphenylurea as a viscous, clear, clorless liquid.

Workup

customat 45°-50° C
extractionThe mixture is extracted with methylene chloride
customthe extract is evaporated
customThe residue is purified by chromatography
customAfter evaporation of the eluent
distillationthe residue is evaporatively distilled at 165° C. under reduced pressure (150 microns)

Sources & evidence

ORD record: ord-e3fdeaf7808b43a99a6068719c6a001b
Source dataset: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04473579

Reaction notes

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