Phenyl isocyanate → HCID 18008921, compound

HRID 987487Notes

Reaction equation

HRID 987487 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH:16]=[C:15]([CH2:17][OH:18])[N:14]=[CH:13]1)[N:8]=[C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:6](=[O:24])[NH:5]2.[C:25]1([N:31]=[C:32]=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH:16]=[C:15]([CH2:17][O:18][C:32](=[O:33])[NH:31][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:14]=[CH:13]1)[N:8]=[C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:6](=[O:24])[NH:5]2

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 18008902HCID 18008902, compound

Product 1

HCID 18008921HCID 18008921, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of the compound (100 mg, 287 μmol) of Example 41 in ethyl acetate (3 ml) were added phenyl isocyanate (68.4 mg, 574 μmol) and triethylamine (58.1 mg, 574 μmol), and the mixture was refluxed for 24 hours. After cooling, the insolubles were filtered off and solvent was distilled off. The residue obtained was purified by means of silica gel column chromatography [ethyl acetate], thereby obtaining 76.0 mg of title compound as light brown powder. Yield 57%.

Workup

  1. temperaturethe mixture was refluxed for 24 hours
  2. temperatureAfter cooling
  3. filtrationthe insolubles were filtered off
  4. distillationsolvent was distilled off
  5. customThe residue obtained
  6. customwas purified by means of silica gel column chromatography [ethyl acetate]

Sources & evidence

ORD record
ord-83b84f71125b43cc9e9e07078883988d
Source dataset
uspto-grants-2003_10
Patent number
US06632813B1

Reaction notes

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