1-Chloroethyl chloroformate → HCID 21890637, compound

HRID 721481Notes

Reaction equation

HRID 721481 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]3[C:34]4[C:29](=[CH:30][C:31]([O:37][CH3:38])=[C:32]([O:35][CH3:36])[CH:33]=4)[N:28]=[CH:27][CH:26]=3)=[CH:20][CH:19]=2)=[O:16])[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClCCCl>[CH3:36][O:35][C:32]1[CH:33]=[C:34]2[C:29](=[CH:30][C:31]=1[O:37][CH3:38])[N:28]=[CH:27][CH:26]=[C:25]2[O:24][C:21]1[CH:22]=[CH:23][C:18]([NH:17][C:15]([NH:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[O:16])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 21891103HCID 21891103, compound

Product 1

HCID 21890637HCID 21890637, compoundYield 168.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

N-(1-Benzyl-4-piperidyl)-N′-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}urea (100 mg) was dissolved in 1,2-dichloroethane (25 ml) to prepare a solution. 1-Chloroethyl chloroformate (0.10 ml) was then added to the solution, and the mixture was heated under reflux overnight. The solvent was removed by distillation under the reduced pressure. Methanol (20 ml) was added to the residue, followed by heating under reflux for 2 hr. The solvent was removed by distillation under the reduced pressure to give 139 mg of N-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-N′-(4-piperidyl)urea (1).

Workup

  1. customto prepare a solution
  2. temperaturethe mixture was heated
  3. temperatureunder reflux overnight
  4. customThe solvent was removed by distillation under the reduced pressure
  5. additionMethanol (20 ml) was added to the residue
  6. temperatureby heating
  7. temperatureunder reflux for 2 hr
  8. customThe solvent was removed by distillation under the reduced pressure

Sources & evidence

ORD record
ord-17e16baf2d6944e6a9a470882bd4b286
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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