3-Chloro-4-methylphenyl isocyanate → HCID 22186081, compound

HRID 1837502Notes

Reaction equation

HRID 1837502 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[N:10]1[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]1.[Cl:17][C:18]1[CH:19]=[C:20]([N:25]=[C:26]=[O:27])[CH:21]=[CH:22][C:23]=1[CH3:24]>C1(C)C=CC=CC=1>[ClH:17].[Cl:17][C:18]1[CH:19]=[C:20]([NH:25][C:26]([NH:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([N:10]3[CH2:11][CH2:12][N:13]([CH3:16])[CH2:14][CH2:15]3)[CH:5]=2)=[O:27])[CH:21]=[CH:22][C:23]=1[CH3:24]

Participants

4

Reactant 2

HCID 628323-Chloro-4-methylphenyl isocyanateHCID 103311014-Methoxy-3-(4-methylpiperazin-1-yl)aniline

Product 1

HCID 22186081HCID 22186081, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 13.6 mmol (3 g) of 4-methoxy-3-(4-methyl-1-piperazinyl)phenylamine and 13.6 mmol (2.26 g) of 3-chloro-4-methylphenyl isocyanate in 100 ml of toluene is heated at reflux for 2 hours. After cooling, the precipitate obtained is filtered off, and rinsed twice with diethyl ether. The solid obtained is purified by chromatography on silica gel, using as eluant a 96/4/0.4 dichloromethane/methanol/ammonium hydroxide mixture, to yield the expected product. The corresponding hydrochloride is obtained by the action of an ethanolic HCl solution.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 2 hours
  3. temperatureAfter cooling
  4. customthe precipitate obtained
  5. filtrationis filtered off
  6. washrinsed twice with diethyl ether
  7. customThe solid obtained
  8. customis purified by chromatography on silica gel

Sources & evidence

ORD record
ord-dadfef3e86ce4f078d26979a2bda101a
Source dataset
uspto-grants-2004_08
Patent number
US06784183B2

Reaction notes

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