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

HRID 2225942Notes

Reaction equation

HRID 2225942 reaction equation
[CH:1]1(Br)[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([OH:15])=[CH:10][C:9]=1[NH:16][C:17](=[O:20])[O:18][CH3:19].C(=O)([O-])[O-].[K+].[K+].Cl>C(#N)C>[F:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([O:15][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:10][C:9]=1[NH:16][C:17](=[O:20])[O:18][CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 19042327methyl N-(2-fluoro-4-chloro-5-hydroxyphenyl)carbamate

Product 1

HCID 15766845methyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamateYield 84.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Cyclopentyl bromide (4.07 g, 27.3 mmol) was added to an acetonitrile solution (50 ml) containing methyl N-(2-fluoro-4-chloro-5-hydroxyphenyl)carbamate (5.00 g, 22,8 mmol) and potassium carbonate (1.80 g, 13.0 mmol), and the mixture was heated under reflux for 4 hours. After reaction, the reaction liquid was cooled to room temperature, 1N hydrochloric acid (50 ml) was added thereto, and this was extracted with ethyl acetate (50 ml×2). The organic layer was washed with water and then dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, and the solvent was removed by distillation under reduced pressure to obtain methyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamate (5.56 g, 19.3 mmol). Yield: 84.8%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. customAfter reaction
  4. customthe reaction liquid
  5. extractionthis was extracted with ethyl acetate (50 ml×2)
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe drying agent was removed by filtration
  9. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-5461178e3dc24cffa08680d3798c41ac
Source dataset
uspto-grants-1994_09
Patent number
US05344953

Reaction notes

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