Ethyl chloroformate → HCID 13457734, compound

HRID 280117Notes

Reaction equation

HRID 280117 reaction equation
[NH2:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)(O)[O-].[Na+].Cl[C:21]([O:23][CH2:24][CH3:25])=[O:22]>ClCCl>[C:7]([C:3]1[N:2]([NH:1][C:21](=[O:22])[O:23][CH2:24][CH3:25])[CH:6]=[CH:5][CH:4]=1)(=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 13457732HCID 13457732, compound

Product 1

HCID 13457734HCID 13457734, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 1-amino-2-benzoylpyrrole (12.3 g, 66 mmol) and sodium bicarbonate (13.9 g, 165 mmol) in 250 ml of dichloromethane was added a solution of ethyl chloroformate (8.2 g, 75 mmol) in 50 ml of dichloromethane. This mixture was stirred at reflux for 5 hours and then quenched with 150 ml of ice. The dichloromethane layer was separated, washed with water, dried over anhydrous Na2SO4, filtered and evaporated to an oil. This oil solidified upon trituration with hexane to give 16.3 g (96%) of powder, m.p. 68°-70°.

Workup

  1. temperatureat reflux for 5 hours
  2. customquenched with 150 ml of ice
  3. customThe dichloromethane layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated to an oil

Sources & evidence

ORD record
ord-acd77706d035497e9567557f9e15fa71
Source dataset
uspto-grants-1986_05
Patent number
US04588727

Reaction notes

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