Hydrochloric Acid → N-[4-Chloro-5-(cyclopentyloxy)-2-fluorophenyl]carbamic acid ethyl ester

HRID 21473

Reaction equation

HRID 21473 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][C:10](OC)=O)=[CH:4][C:3]=1[NH:14][C:15](=[O:19])[O:16][CH2:17][CH3:18].C(=O)([O-])[O-].[K+].[K+].[CH:26]1(Br)[CH2:30]C[CH2:28][CH2:27]1.Cl>C(O)C>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]2[CH2:28][CH2:27][CH2:26][CH2:30]2)=[CH:4][C:3]=1[NH:14][C:15](=[O:19])[O:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 19374489ethyl N-(2-fluoro-4-chloro-5-methoxycarbonyloxyphenyl)carbamate

Product 1

HCID 11033971N-[4-Chloro-5-(cyclopentyloxy)-2-fluorophenyl]carbamic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl N-(2-fluoro-4-chloro-5-methoxycarbonyloxyphenyl)carbamate (1.45 g, 4.97 mmol) prepared by the process described in Reference Example 1 and a solution of potassium carbonate (1.03 g, 7.46 mmol) in ethanol (5.0 ml) were stirred for 1 hour while refluxing, and then cyclopentyl bromide (1.11 g, 7.46 mmol) was added thereto, followed by further stirring for 2 hours. After completion of the reaction, the mixture was poured into 1N hydrochloric acid (50 ml), and extracted with ethyl acetate (50 ml×3 times). The organic layer was dried, and concentrated under reduced pressure to obtain ethyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamate as grey white crystals (1.41 g, 4 69 mmol 94.4% yield) The spectral data and the like are as shown in Reference Example 1.

Workup

  1. temperaturewhile refluxing
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate (50 ml×3 times)
  4. customThe organic layer was dried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9d0abb7cc6254bdbb0310c2c9d07c792
Source dataset
uspto-grants-1995_06
Patent number
US05424277

Linked notes

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