Diphosgene → 4-Chloro-5-cyclopentyloxy-2-fluorophenylisocyanate

HRID 275100Notes

Reaction equation

HRID 275100 reaction equation
Cl[C:2](OC(Cl)(Cl)Cl)=[O:3].[F:9][C:10]1[CH:16]=[C:15]([Cl:17])[C:14]([O:18][CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:13][C:11]=1[NH2:12]>C(OCC)(=O)C>[F:9][C:10]1[CH:16]=[C:15]([Cl:17])[C:14]([O:18][CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:13][C:11]=1[N:12]=[C:2]=[O:3]

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 152793894-Chloro-5-(cyclopentyloxy)-2-fluorobenzenamine

Product 1

HCID 544415444-Chloro-5-cyclopentyloxy-2-fluorophenylisocyanate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

An ethyl acetate solution (5 ml) of trichloromethyl chloroformate (2.00 g, 10.0 mmol) was gradually dropwise added to an ethyl acetate solution (25 ml) of 2-fluoro-4-chloro-5-cyclopentyloxyaniline (2.30 g, 10.0 mmol) at room temperature. After addition, the whole was heated to remove ethyl acetate therefrom by distillation. As a result, 2-fluoro-4-chloro-5-cyclopentyloxyphenylisocyanate was obtained almost quantitatively.

Workup

  1. additionAfter addition
  2. temperaturethe whole was heated
  3. customto remove ethyl acetate
  4. distillationby distillation

Sources & evidence

ORD record
ord-2b2f4343604f4401af1eb6678d38fda0
Source dataset
uspto-grants-1995_02
Patent number
US05391807

Reaction notes

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