Ethyl chloroformate → [2-(2-fluorobenzoyl)-1H-pyrrol-1-yl]carbamic acid, ethyl ester

HRID 280131Notes

Reaction equation

HRID 280131 reaction equation
[NH2:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=[O:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[F:14].C(=O)(O)[O-].[Na+].Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23]>ClCCl>[F:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:7]([C:3]1[N:2]([NH:1][C:22](=[O:23])[O:24][CH2:25][CH3:26])[CH:6]=[CH:5][CH:4]=1)=[O:15]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 134577161-Amino-2-(2-fluorobenzoyl)pyrrole

Product 1

HCID 13457759[2-(2-fluorobenzoyl)-1H-pyrrol-1-yl]carbamic acid, ethyl esterYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Amino-2-(2-fluorobenzoyl)pyrrole (41 g, 0.20 mol) and sodium bicarbonate (39 g, 0.46 mol) were combined in 400 ml of dichloromethane. To this stirred slurry was added ethyl chloroformate (24 g, 0.22 mol) over 3 minutes and the reaction mixture was refluxed for 5 hours, whereupon it was quenched with 200 ml of H2O and the organic layer separated. The organic extract was washed with H2O and brine, dried (MgSO4), filtered, and evaporated to an oil which crystallized upon trituration with hexane. Filtration yielded 50.8 g (92%) of crystals, m.p. 78°-80°.

Workup

  1. temperaturethe reaction mixture was refluxed for 5 hours, whereupon it
  2. customwas quenched with 200 ml of H2O
  3. customthe organic layer separated
  4. extractionThe organic extract
  5. washwas washed with H2O and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated to an oil which
  9. customcrystallized upon trituration with hexane
  10. filtrationFiltration

Sources & evidence

ORD record
ord-440dd49913d7410eb93bed8edd54f69a
Source dataset
uspto-grants-1986_05
Patent number
US04588727

Reaction notes

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