n-Heptyl isocyanate → methyl (Z)-3-[2-butoxy-3'-(3-heptylureido)biphenyl-4-yl]-2-methoxyacrylate

HRID 390693Notes

Reaction equation

HRID 390693 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11](/[CH:14]=[C:15](\[O:20][CH3:21])/[C:16]([O:18][CH3:19])=[O:17])=[CH:10][C:9]=2[O:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:5]=[CH:6][CH:7]=1.[CH2:27]([N:34]=[C:35]=[O:36])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>CCOCC>[CH2:23]([O:22][C:9]1[CH:10]=[C:11](/[CH:14]=[C:15](\[O:20][CH3:21])/[C:16]([O:18][CH3:19])=[O:17])[CH:12]=[CH:13][C:8]=1[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:35]([NH:34][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[O:36])[CH:3]=1)[CH2:24][CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 138341n-Heptyl isocyanateHCID 86626122methyl (Z)-3-(3'-amino-2-butoxybiphenyl-4-yl)-2-methoxyacrylate

Product 1

HCID 86626123methyl (Z)-3-[2-butoxy-3'-(3-heptylureido)biphenyl-4-yl]-2-methoxyacrylateYield 79%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

376 mg (1.1 mmol) of methyl (Z)-3-(3′-amino-2-butoxybiphenyl-4-yl)-2-methoxyacrylate and 0.3 mL (2.2 mmol) of heptyl isocyanate are heated at 100° C. by microwave in an Emrys Optimizer machine for 20 minutes. The residue obtained is taken up in ether and then filtered by suction. 431 mg (79%) of methyl (Z)-3-[2-butoxy-3′-(3-heptylureido)biphenyl-4-yl]-2-methoxyacrylate are obtained in the form of a white powder.

Workup

  1. customThe residue obtained
  2. filtrationfiltered by suction

Sources & evidence

ORD record
ord-db3beff08bae46f09fef1acc2c5c9e6f
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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