3,5-Bis(trifluoromethyl)phenyl isocyanate → 4-[3-(3,5-Bis(trifluoromethyl)phenyl)-1-(4-cyclohexylphenyl)ureidomethyl]benzoic acid methyl ester

HRID 412429Notes

Reaction equation

HRID 412429 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.[F:25][C:26]([F:41])([F:40])[C:27]1[CH:28]=[C:29]([N:37]=[C:38]=[O:39])[CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:5]=[CH:6][C:7]([CH2:10][N:11]([C:12]2[CH:13]=[CH:14][C:15]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:16][CH:17]=2)[C:38]([NH:37][C:29]2[CH:30]=[C:31]([C:33]([F:35])([F:36])[F:34])[CH:32]=[C:27]([C:26]([F:25])([F:40])[F:41])[CH:28]=2)=[O:39])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 27333143,5-Bis(trifluoromethyl)phenyl isocyanateHCID 67483208Methyl 4-(((4-cyclohexylphenyl)amino)methyl)benzoate

Product 1

HCID 865860584-[3-(3,5-Bis(trifluoromethyl)phenyl)-1-(4-cyclohexylphenyl)ureidomethyl]benzoic acid methyl esterYield 101%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-((4-Cyclohexylphenylamino)methyl)benzoic acid methyl ester (2.38 g, 7.36 mmol) was dissolved in DCM (150 mL) and 3,5-bis(trifluoromethyl)phenyl isocyanate (1.36 mL, 8.10 mmol) was added and the mixture was stirred at room temperature for 16 hours. The reaction mixture was washed with water (3×15 mL), dried (magnesium sulphate) and concentrated in vacuo to afford 4.3 g of 4-[3-(3,5-bis(trifluoromethyl)phenyl)-1-(4-cyclohexylphenyl)ureidomethyl]benzoic acid methyl ester.

Workup

  1. washThe reaction mixture was washed with water (3×15 mL)
  2. dry with materialdried (magnesium sulphate)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b2ff9bdf0e784a9bb7a15ce8f71f8f41
Source dataset
uspto-grants-2003_05
Patent number
US06562807B2

Reaction notes

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