Hydrochloric Acid → benzyl N-(2-fluoro-4-chloro-5-methoxycarbonyloxyphenyl)carbamate

HRID 21486Notes

Reaction equation

HRID 21486 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:6]([O:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][C:3]=1[NH2:4].C(=O)([O-])[O-].[K+].[K+].Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23].Cl>CC(C)=O>[F:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:6]([O:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][C:3]=1[NH:4][C:22](=[O:23])[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 107989305-Amino-2-chloro-4-fluorophenyl methyl carbonate

Product 1

HCID 19374478benzyl N-(2-fluoro-4-chloro-5-methoxycarbonyloxyphenyl)carbamateYield 91.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Fluoro-4-chloro-5-methoxycarbonyloxyaniline (2.00 g, 6.86 mmol), potassium carbonate (1.42 g, 10.3 mmol), benzyl chloroformate (1.17 g, 6.86 mmol) and acetone (20 ml) as a solvent were charged into a 100 cc two-necked flask, and heated for 2 hours while refluxing. After completion of the reaction, the mixture was added to 1H hydrochloric acid (50 ml), and extracted with ethyl acetate (50 ml×3). After drying, the organic layer was concentrated to obtain substantially pure benzyl N-(2-fluoro-4-chloro-5-methoxycarbonyloxyphenyl)carbamate as a solid (2.21 g, 91.1% yield).

Workup

  1. temperatureheated for 2 hours
  2. temperaturewhile refluxing
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate (50 ml×3)
  5. customAfter drying
  6. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-24393e1d720f4d3f907623e90df8f15c
Source dataset
uspto-grants-1995_06
Patent number
US05424277

Reaction notes

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