Ethyl chloroformate → HCID 13457750, compound

HRID 462748Notes

Reaction equation

HRID 462748 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[Cl:14].C(=O)(O)[O-].[Na+].Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23]>ClCCl>[Cl: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 13457740HCID 13457740, compound

Product 1

HCID 13457750HCID 13457750, compoundYield 120.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Amino-2-(2-chlorobenzoyl)pyrrole (32 g, 0.145 mol) was combined with sodium bicarbonate (30.2 g, 0.36 mol) in 400 ml of dichloromethane. To this rapidly stirred mixture was added ethyl chloroformate (18.6 g, 0.172 mol) over 2 minutes and the resultant slurry heated under reflux for 2.5 hours. The reaction mixture was quenched with 300 ml of H2O, separated, washed with H2O, dried (MgSO4), filtered, and evaporated to give 51 g of an oil. This oil was purified by HPLC (silica, 10:1 DCM-ethyl acetate) to give after evaporation 32.8 g (77%) of crystals, m.p. 90°-92°.

Workup

  1. temperaturethe resultant slurry heated
  2. temperatureunder reflux for 2.5 hours
  3. customThe reaction mixture was quenched with 300 ml of H2O
  4. customseparated
  5. washwashed with H2O
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-a99b720a5ded444b9585e9e8f2e0ec43
Source dataset
uspto-grants-1985_05
Patent number
US04517195

Reaction notes

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