Ethyl chloroformate → HCID 13457764, compound

HRID 280136Notes

Reaction equation

HRID 280136 reaction equation
[NH2:1][N:2]1[C:6]([CH3:7])=[CH:5][CH:4]=[C:3]1[C:8](=[O:16])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:15].C(=O)(O)[O-].[Na+].Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24]>ClCCl>[Cl:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:8]([C:3]1[N:2]([NH:1][C:23](=[O:24])[O:25][CH2:26][CH3:27])[C:6]([CH3:7])=[CH:5][CH:4]=1)=[O:16]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 13457763HCID 13457763, compound

Product 1

HCID 13457764HCID 13457764, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred slurry containing 1-amino-2-(2-chlorobenzoyl)-5-methylpyrrole (27.1 g, 0.115 mol) and sodium bicarbonate (16.8 g, 0.20 mol) in 300 ml of dichloromethane was added ethyl chloroformate (21.7 g, 0.20 mol) over 5 minutes. The reaction mixture was stirred at room temperature overnight and thereafter quenched with 500 ml of H2O. The organic layer was washed with brine, dried (MgSO4), charcoaled, filtered, and evaporated to an oil. This oil crystallized in hexane, which was recrystallized from ether-hexane to give 31.9 g (90%) of powder, m.p. 82°-84°.

Workup

  1. customquenched with 500 ml of H2O
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to an oil
  6. customThis oil crystallized in hexane
  7. customwhich was recrystallized from ether-hexane

Sources & evidence

ORD record
ord-1e4440b56f374edb9474d95ebb9e4c89
Source dataset
uspto-grants-1986_05
Patent number
US04588727

Reaction notes

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