p-(Trifluoromethoxy)phenyl isocyanate → HCID 53639517, compound

HRID 1633961Notes

Reaction equation

HRID 1633961 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11]C2CCC(C(O)=O)CC2)=[CH:6][CH:5]=1.[F:22][C:23]([F:35])([F:34])[O:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]=[C:32]=[O:33])=[CH:27][CH:26]=1>C(#N)C>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:5]=[CH:6][C:7]([CH:10]([NH:11][C:32]([NH:31][C:28]2[CH:27]=[CH:26][C:25]([O:24][C:23]([F:34])([F:35])[F:22])=[CH:30][CH:29]=2)=[O:33])[CH:7]2[CH2:8][CH2:9][CH:4]([C:3]([OH:21])=[O:2])[CH2:5][CH2:6]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 92298p-(Trifluoromethoxy)phenyl isocyanateHCID 54072366HCID 54072366, compound

Product 1

HCID 53639517HCID 53639517, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

The above 4-[(4-carboxycyclohexylamino)methyl]benzoic acid methyl ester (1 g, 3.4 mmol) was dissolved in acetonitrile (25 mL) and 4-trifluoromethoxyphenylisocyanate (0.73 g, 3.4 mmol) was added. Stirring overnight at 50° C. followed by cooling to 25° C. formed a precipitate, which was removed by filtration. The filtrate was concentrated in vacuo and the product purified by chromatography using silica as stationary phase and a mixture of ethyl acetate, methanol and acetic acid as eluent (15:1:0.1).

Workup

  1. temperatureby cooling to 25° C.
  2. customformed a precipitate, which
  3. customwas removed by filtration
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe product purified by chromatography
  6. additiona mixture of ethyl acetate, methanol and acetic acid as eluent (15:1:0.1)

Sources & evidence

ORD record
ord-ca27c553327a4d40b568d14a61579655
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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