Toluene → HCID 67272939, compound

HRID 250879Notes

Reaction equation

C1(P(=[CH:20][C:21]([O:23][CH3:24])=[O:22])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:25]([N:27]([C:38]1[CH:39]=[C:40]([C:44]2[CH:49]=[CH:48][C:47](C=O)=[CH:46][CH:45]=2)[CH:41]=[CH:42][CH:43]=1)[C:28]([NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[O:29])[CH3:26].[C:52]1(C)C=CC=CC=1>>[CH2:25]([N:27]([C:38]1[CH:39]=[C:40]([C:44]2[CH:49]=[CH:48][C:47](/[CH:52]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])=[CH:46][CH:45]=2)[CH:41]=[CH:42][CH:43]=1)[C:28]([NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[O:29])[CH3:26]

Participants

Reactant 3

HCID 1140Toluene

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester

HCID 86223658HCID 86223658, compound

Product 1

HCID 67272939HCID 67272939, compoundYield 91%

Conditions

Temperature: 90 °C

Procedure

1.0 g (3 mmol, 1.5 eq) of methyl triphenylphosphoranylideneacetate are added to a solution of 740 mg (2.02 mmol, 1 eq) of 1-ethyl-1-(4′-formylbiphenyl-3-yl)-3-heptylurea in 8 ml of toluene. The reaction mixture is heated at 90° C. for 1 hour. The solvent is evaporated off and the residual oil is then chromatographed on silica gel (8/2 heptane/ethyl acetate). 775 mg of methyl (E)-3-[3′-(1-ethyl-3-heptylureido)biphenyl-4-yl]acrylate are obtained in the form of an off-white solid. Yield=91%

Workup

customThe solvent is evaporated off
customthe residual oil is then chromatographed on silica gel (8/2 heptane/ethyl acetate)

Sources & evidence

ORD record: ord-3d334c24a23a4559af23b82925dbb468
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863332B2

Reaction notes

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