Ethyl chloroformate → HCID 14601944, compound

HRID 2072695Notes

Reaction equation

HRID 2072695 reaction equation
C(=O)(O)[O-].[Na+].[NH2:6][N:7]1[CH:11]=[CH:10][CH:9]=[CH:8]1.Cl[C:13]([O:15][CH2:16][CH3:17])=[O:14]>ClCCl>[CH2:16]([O:15][C:13](=[O:14])[NH:6][N:7]1[CH:11]=[CH:10][CH:9]=[CH:8]1)[CH3:17]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 1365891-AminopyrroleHCID 516892Sodium Bicarbonate

Product 1

HCID 14601944HCID 14601944, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 15 g of sodium bicarbonate and 9.2 g of (N-amino)pyrrole in 50 ml of dichloromethane was treated over a period of fifteen minutes with 11.4 ml of ethyl chloroformate. The reaction mixture was then stirred at ambient temperature for four hours and filtered. The filtrate was washed with water followed by a saturated solution of sodium chloride, dried over anhydrous magnesium sulfate, and filtered. Concentration afforded 17 g of N-(1H-pyrrol-1-yl)carbamic acid ethyl ester, m.p. 60°-61° C.; MS(EI)M+ @154(100%); IR(CHCl3)--NH @ 3430 cm1, C=O @ 1755 cm-1.

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationConcentration

Sources & evidence

ORD record
ord-95edc9a62339484cabf2b2147436eb7f
Source dataset
uspto-grants-1990_04
Patent number
US04914103

Reaction notes

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