Hydrochloric Acid → HCID 13370096, compound

HRID 236352Notes

Reaction equation

HRID 236352 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.[C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:10].P(C#N)(=O)(OCC)OCC.Cl>CN(C)C=O.O.C(N(CC)CC)C>[O:8]=[C:6]([C:2]1[NH:1][CH:5]=[CH:4][CH:3]=1)[CH:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:9]#[N:10]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7764Ethyl cyanoacetateHCID 12473Pyrrole-2-Carboxylic AcidHCID 76257Diethyl cyanophosphonate

Product 1

HCID 13370096HCID 13370096, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 2.2 g of pyrrole-2-carboxylic acid, 8.4 ml of anhydrous triethylamine and 2.1 ml of ethyl cyanoacetate in dimethylformamide is treated with 2.9 ml of diethyl phosphorocyanidate at room temperature. After stirring for 80 minutes at room temperature, the reaction mixture is cooled in an ice bath, treated with about 50 ml of water and acidified with 6N hydrochloric acid. The crude precipitate is collected, washed with water, dried and recrystallized from ether to yield β-oxo-α-ethoxycarbonyl-β-(2-pyrrolyl)-propionitrile, m.p. 138°-9°.

Workup

  1. temperaturethe reaction mixture is cooled in an ice bath
  2. customThe crude precipitate is collected
  3. washwashed with water
  4. customdried
  5. customrecrystallized from ether

Sources & evidence

ORD record
ord-827af495c62741e8b3c14c146850c3ac
Source dataset
uspto-grants-1987_02
Patent number
US04644010

Reaction notes

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