4-Chlorophenyl Isocyanate → HCID 22185489, compound

HRID 1795145Notes

Reaction equation

HRID 1795145 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.[NH2:11][CH2:12][C:13]([C:16]1[NH:17][C:18]([C:29]2[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=2)=[C:19]([C:21]2[CH:22]=[CH:23][C:24]([Cl:28])=[C:25]([OH:27])[CH:26]=2)[N:20]=1)([CH3:15])[CH3:14]>ClCCl.CO>[Cl:28][C:24]1[CH:23]=[CH:22][C:21]([C:19]2[N:20]=[C:16]([C:13]([CH3:14])([CH3:15])[CH2:12][NH:11][C:9]([NH:8][C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)=[O:10])[NH:17][C:18]=2[C:29]2[CH:30]=[CH:31][N:32]=[CH:33][CH:34]=2)=[CH:26][C:25]=1[OH:27]

Participants

5

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 22185475HCID 22185475, compound

Product 1

HCID 22185489HCID 22185489, compoundYield 48.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-chlorophenylisocyanate (46 mg, 0.3 mmol) in dichloromethane (5 ml) was treated with a solution of Example 3 (103 mg, 0.3 mmol) in methanol (1 ml). After stirring at room temperature for 30 min the solution was concentrated under reduced pressure and the residue chromatographed on silica gel eluting with dichloromethane/methanol (10:1) to the give the title compound (72 mg, 48%) as a pale yellow solid; MS(ES+) m/e 496/498/500 [M+H]+.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customthe residue chromatographed on silica gel eluting with dichloromethane/methanol (10:1) to the

Sources & evidence

ORD record
ord-ecb38d041c8e409580822d83242b7cab
Source dataset
uspto-grants-2006_04
Patent number
US07026336B1

Reaction notes

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