Phenyl isocyanate → HCID 18008911, compound

HRID 987484Notes

Reaction equation

HRID 987484 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:8]=[CH:7][N:6]([C:9]2[CH:18]=[C:17]3[C:12]([NH:13][C:14](=[O:24])[CH:15]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[NH:16]3)=[CH:11][C:10]=2[Cl:25])[CH:5]=1.[C:26]1([N:32]=[C:33]=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)CC)C>CN(C)C=O>[Cl:25][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:9]=1[N:6]1[CH:7]=[CH:8][C:4]([CH2:3][NH:2][C:33]([NH:32][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:34])=[CH:5]1)[N:16]=[C:15]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14](=[O:24])[NH:13]2

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471Triethylamine2×HCID 18008893HCID 18008893, compound

Product 1

HCID 18008911HCID 18008911, compoundYield 26.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the compound (200 mg, 519 μmol) of Example 5 in N,N-dimethylformamide (5 ml) were added phenyl isocyanate (67.6 μl, 622 μmol) and successively triethylamine (108 μl, 778 μmol), and the mixture was stirred for 1 hour at 60° C. Triethylamine (723 μl, 5.19 mmol) was added to the reaction mixture, which was stirred for 4 hours at 100° C. The residue obtained by concentrating the reaction mixture under reduced pressure was submitted to silica gel column chromatography [dichloromethane-ethanol=20:1] to obtain 64.1 mg of title compound as yellow powder. Yield 26%.

Workup

  1. stirringwas stirred for 4 hours at 100° C
  2. customThe residue obtained
  3. concentrationby concentrating the reaction mixture under reduced pressure

Sources & evidence

ORD record
ord-db2a3e9909ba430da8b6a1900d8d4a10
Source dataset
uspto-grants-2003_10
Patent number
US06632813B1

Reaction notes

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