Hydrochloric Acid → methyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamate

HRID 1720427Notes

Reaction equation

HRID 1720427 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[CH:4][C:3]=1[NH:10][C:11](=[O:14])[O:12][CH3:13].[CH:15]1(OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:19][CH2:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+].Cl>CC(C)=O.[I-].[K+]>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:4][C:3]=1[NH:10][C:11](=[O:14])[O:12][CH3:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 317685Cyclopentyl 4-methylbenzene-1-sulfonateHCID 19042327methyl N-(2-fluoro-4-chloro-5-hydroxyphenyl)carbamate

Product 1

HCID 15766845methyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamateYield 93.1%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent

Procedure

Methyl N-(2-fluoro-4-chloro-5-hydroxyphenyl)carbamate (1.64 Kg, 7.47 mol), cyclopentyl-p-toluenesulfonate (1.80 Kg, 7.48 mol), potassium carbonate (1.03 Kg, 7.46 mol) and potassium iodide (12.3 g, 1.0 mol %) were placed in a 101 three-necked flask equipped with a stirrer and a Dimroth funnel, and, after adding acetone (7.5 liters) as a solvent thereto, the mixture was refluxed under heating for 4 hours. After completion of the reaction, the reaction solution was taken out, and 0.5 N hydrochloric acid (20 liters) was added thereto while vigorously stirring. The precipitated methyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamate as a white solid (2.0 Kg, 6.95 mol, 93.1% yield ) was isolated by filtration and thoroughly dired.

Workup

  1. customequipped with a stirrer
  2. temperaturethe mixture was refluxed
  3. temperatureunder heating for 4 hours
  4. customAfter completion of the reaction

Sources & evidence

ORD record
ord-8d505d331ab647ea9e6fe6c69479999c
Source dataset
uspto-grants-1996_04
Patent number
US05506190

Reaction notes

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