Hydrochloric Acid → methyl N-{2-fluoro-4-chloro-5-(3-methylcyclopentyl)oxyphenyl}carbamate

HRID 21476Notes

Reaction equation

HRID 21476 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][C:10](OCC(C)C)=O)=[CH:4][C:3]=1[NH:17][C:18](=[O:21])[O:19][CH3:20].[C:22]1([CH3:38])[CH:27]=CC(S(OC2CCC(C)C2)(=O)=O)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CO>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]2[CH2:24][CH2:23][CH:22]([CH3:38])[CH2:27]2)=[CH:4][C:3]=1[NH:17][C:18](=[O:21])[O:19][CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 190423383-Methylcyclopentyl 4-methylbenzene-1-sulfonateHCID 19374471methyl N-(2-fluoro-4-chloro-5-isobutyloxycarbonyloxyphenyl)carbamate

Product 1

HCID 19374472methyl N-{2-fluoro-4-chloro-5-(3-methylcyclopentyl)oxyphenyl}carbamateYield 75.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl N-(2-fluoro-4-chloro-5-isobutyloxycarbonyloxyphenyl)carbamate (5.37 g, 16.8 mmol) prepared by the process as shown in Reference Example 3, 3-methylcyclopentyl p-toluenesulfonate (5.0 g, 20.2 mmol) and potassium carbonate (2.32 g, 16.8 mmol) in methanol (50 ml) was stirred for 5 hours under refluxing. After completion of the reaction, the reaction mixture was poured into 1N hydrochloric acid (100 ml), and the mixture was extracted with ethyl acetate (50 ml×3 times). The organic layer was dried, and the solvent was distilled off under reduced pressure to obtain methyl N-{2-fluoro-4-chloro-5-(3-methylcyclopentyl)oxyphenyl}carbamate as grey white crystals (3.81 g, 12.6 mmol, 75.2% yield). 1H-NMR Spectrum (CDCl3, TMS, ppm): δ1.02 and 1.08 (total 3H, d, J=6.0 Hz), 1.25-2.40 (7H, m), 3.77 (3H, s), 4.75 (1H, m), 6.68 (1H, br, s) 7.05 (1H, d, JHF =10.5 Hz), 7.75 (1H, d, JHF =7.5 Hz).

Workup

  1. temperatureunder refluxing
  2. customAfter completion of the reaction
  3. extractionthe mixture was extracted with ethyl acetate (50 ml×3 times)
  4. customThe organic layer was dried
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e7cded928ed540b2954ec7d7adb37b31
Source dataset
uspto-grants-1995_06
Patent number
US05424277

Reaction notes

Loading…