n-Heptyl isocyanate → ethyl (E)-3-[3'-(3-heptyl-1-methylureido)biphenyl-4-yl]-2-methylacrylate

HRID 390651Notes

Reaction equation

HRID 390651 reaction equation
[CH3:1]/[C:2](=[CH:8]\[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][CH3:22])[CH:16]=2)=[CH:11][CH:10]=1)/[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH2:23]([N:30]=[C:31]=[O:32])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>>[CH2:23]([NH:30][C:31](=[O:32])[N:21]([C:17]1[CH:16]=[C:15]([C:12]2[CH:13]=[CH:14][C:9](/[CH:8]=[C:2](\[CH3:1])/[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:10][CH:11]=2)[CH:20]=[CH:19][CH:18]=1)[CH3:22])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

3

Reactant 2

HCID 138341n-Heptyl isocyanateHCID 68957153ethyl (E)-2-methyl-3-(3'-methylaminobiphenyl-4-yl)acrylate

Product 1

HCID 16225425ethyl (E)-3-[3'-(3-heptyl-1-methylureido)biphenyl-4-yl]-2-methylacrylateYield 88%

Procedure

1.0 g (3.4 mmol) of ethyl (E)-2-methyl-3-(3′-methylaminobiphenyl-4-yl)acrylate is mixed with 2 mL of heptyl isocyanate and the medium is irradiated by microwave for 30 minutes at a temperature of 100° C. in an Emrys Optimizer machine. The residue obtained is purified by chromatography on a column of silica eluted with a 9/1 heptane/ethyl acetate mixture. 1.2 g (88%) of ethyl (E)-3-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]-2-methylacrylate are obtained.

Workup

  1. customthe medium is irradiated by microwave for 30 minutes at a temperature of 100° C. in an Emrys Optimizer machine
  2. customThe residue obtained
  3. customis purified by chromatography on a column of silica
  4. washeluted with a 9/1 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-187d1158622940939a16046bf732ce52
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

Loading…