Phenyl isocyanate → HCID 22033724, compound

HRID 1791878Notes

Reaction equation

HRID 1791878 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[NH2:17])[CH:7]=[CH:6][C:5]=1[NH:18][C:19](=[O:22])[CH2:20][CH3:21].[C:24]1([N:30]=[C:31]=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)Cl>[C:24]1([NH:30][C:31](=[O:32])[NH:17][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[O:10][C:8]2[CH:7]=[CH:6][C:5]([NH:18][C:19](=[O:22])[CH2:20][CH3:21])=[C:4]([CH:9]=2)[C:3]([OH:2])=[O:23])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 22033664HCID 22033664, compound

Product 1

HCID 22033724HCID 22033724, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-propionylamino-5-(2-amino-phenoxy)-benzoic acid methyl ester (50.0 mg, 0.153 mmol, prepared as described in EXAMPLE 2) and phenyl isocyanate (21.0 mg, 0.175 mmol) in CH2Cl2 (10 mL) was stirred at room temperature for 2 hours. The solvent was removed by evaporation and the crude ester product was hydrolysed in methanol (1 mL) and 1M NaOH (1 mL) over night. The reaction mixture was acidified with 1M HCl and the product was collected by filtration (54 mg, total yield 80%).

Workup

  1. customThe solvent was removed by evaporation
  2. wait1M NaOH (1 mL) over night
  3. filtrationthe product was collected by filtration (54 mg, total yield 80%)

Sources & evidence

ORD record
ord-84e606289c9f4648b52ded2ff752b4ed
Source dataset
uspto-grants-2006_07
Patent number
US07074831B2

Reaction notes

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