Hydrochloric Acid → 4-Chloro-5-cyclopentyloxy-2-fluorophenylisocyanate

HRID 1278542Notes

Reaction equation

HRID 1278542 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:6]([O:10][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:5][C:3]=1[NH2:4].C(Cl)(=O)[C:17](Cl)=[O:18].Cl>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:6]([O:10][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:5][C:3]=1[N:4]=[C:17]=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 152793894-Chloro-5-(cyclopentyloxy)-2-fluorobenzenamine

Product 1

HCID 544415444-Chloro-5-cyclopentyloxy-2-fluorophenylisocyanateYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 2-fluoro-4-chloro-5-cyclopentyloxyaniline (1.0 g, 5 mmol) in toluene (50 mL) was added dropwise to a solution of oxalyl chloride (2.0 g, 10 mmol) in toluene (20 mL) with stirring. The reaction mixture was stirred at room temperature for 1 hour and then heated to reflux for 4 hours until HCl evolution ceased. The mixture was cooled down to room temperature and the solvents were removed at reduced pressure to give 1.1 g of 2-fluoro-4-chloro-5-cylcopentyloxyphenyl isocyanate as an oily product. This was used in the next step without further purification.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 hour
  2. temperatureheated
  3. customthe solvents were removed at reduced pressure

Sources & evidence

ORD record
ord-eaa96b30c2e14c0296c337f5edba84f2
Source dataset
uspto-grants-2002_09
Patent number
US06444615B1

Reaction notes

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