Phenethyl isocyanate → methyl (Z)-3-[2-butoxy-3'-(1-methyl-3-phenethylureido)biphenyl-4-yl]-2-ethoxyacrylate

HRID 390633Notes

Reaction equation

HRID 390633 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[C:10](/[CH:12]=[C:13](\[O:18][CH2:19][CH3:20])/[C:14]([O:16][CH3:17])=[O:15])[CH:9]=[CH:8][C:7]=1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([NH:27][CH3:28])[CH:22]=1)[CH2:2][CH2:3][CH3:4].[CH2:29]([N:37]=[C:38]=[O:39])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[CH2:1]([O:5][C:6]1[CH:11]=[C:10](/[CH:12]=[C:13](\[O:18][CH2:19][CH3:20])/[C:14]([O:16][CH3:17])=[O:15])[CH:9]=[CH:8][C:7]=1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N:27]([CH3:28])[C:38]([NH:37][CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:39])[CH:22]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 160602Phenethyl isocyanateHCID 86626091methyl (Z)-3-(2-butoxy-3'-methylaminobiphenyl-4-yl)-2-ethoxyacrylate

Product 1

HCID 86626092methyl (Z)-3-[2-butoxy-3'-(1-methyl-3-phenethylureido)biphenyl-4-yl]-2-ethoxyacrylateYield 75.4%

Procedure

40 mg (0.1 mmol) of methyl (Z)-3-(2-butoxy-3′-methylaminobiphenyl-4-yl)-2-ethoxyacrylate and 16 mg (0.11 mmol) phenethyl isocyanate are heated at 85° C. by microwave in an Emrys Optimizer machine for 20 minutes. The residue obtained is purified by chromatography on a column of silica eluted with a 95/5 and then 90/10 heptane/ethyl acetate mixture. 40 mg (72%) of methyl (Z)-3-[2-butoxy-3′-(1-methyl-3-phenethylureido)biphenyl-4-yl]-2-ethoxyacrylate are obtained.

Workup

  1. customThe residue obtained
  2. customis purified by chromatography on a column of silica
  3. washeluted with a 95/5

Sources & evidence

ORD record
ord-658eb63e616e486d97fc242f9f5c165e
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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