Ethyl chloroformate → 1-(4-Ethoxycarbonylaminophenyl)pyrrole

HRID 1167463Notes

Reaction equation

HRID 1167463 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[CH:17][CH:16]=[CH:15]2)=[CH:10][CH:9]=1>N1C=CC=CC=1>[CH2:5]([O:4][C:2]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH:18]=[CH:17][CH:16]=[CH:15]2)=[CH:12][CH:13]=1)=[O:3])[CH3:6]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 27954574-Pyrrol-1-yl-phenylamine

Product 1

HCID 149198291-(4-Ethoxycarbonylaminophenyl)pyrrole

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ethyl chloroforrnate (0.38 ml) was added dropwisc to a stirred solution of 1-(4-aminophenyl)pyrrole (0.56 g, 3.54 mmol , Corelli et al., Farmaco. Ed. Sci., 1983, 38, 219) in pyridine (5 ml) at 5-10° C. for 15 minutes. The cooling bath was removed and stirring continued for 1.5 hours. The mixture was evaporated and the residue was purified by flash column chromatography on silica gel, eluting with a gradient of 1-4% MeOH in dichloromethane to give the title product (0.43 g) as a solid.

Workup

  1. customThe cooling bath was removed
  2. customThe mixture was evaporated
  3. customthe residue was purified by flash column chromatography on silica gel
  4. washeluting with a gradient of 1-4% MeOH in dichloromethane

Sources & evidence

ORD record
ord-1ed62850dab7449f904cee0391797b40
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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