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

HRID 742431

Reaction equation

HRID 742431 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 10L 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 for4 hours. After completion of the reaction, the reaction solution was taken out, and 0.5N 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 for4 hours
  4. customAfter completion of the reaction

Sources & evidence

ORD record
ord-2a4e3ab8cf6c471282fa64238545f162
Source dataset
uspto-grants-1996_09
Patent number
US05554581

Linked notes

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