Hydrochloric Acid → HCID 23347801, compound

HRID 1855719Notes

Reaction equation

HRID 1855719 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].Cl.C[N:15]1C=CC=C1.C(C(OCC)=O)#N.C(=O)(O)[O-].[Na+]>C(O)C>[NH:15]=[C:7]([C:3]1[N:2]([CH3:1])[CH:6]=[CH:5][CH:4]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 73041-MethylpyrroleHCID 69336Ethyl cyanoformateHCID 974691H-Pyrrole-2-acetic acid, 1-methyl-, ethyl esterHCID 516892Sodium Bicarbonate

Product 1

HCID 23347801HCID 23347801, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 1-methylpyrrole-2-acetate: A stream of dry hydrogen chloride is passed at a moderate rate through a solution of 12.5 g of N-methylpyrrole and 16.8 g of ethyl cyanoformate in 125 mls of ethanol-free chloroform at 22° C. for 31/2 hours. The reaction mixture is added dropwise with stirring to a 1.5 liter solution of 5% sodium bicarbonate. The chloroform layer is separated, dried over Na2SO4 and evaporated in vacuo at room temperature to give a brown oil (ethyl α-imino-1-methylpyrrole-2-acetate). The oil is dissolved in 125 ml of ethanol. Hydrogen sulfide is passed through the solution vigorously for 45 mins at 22° C. The mixture is allowed to stand for 16 hrs. The solvent is evaporated in vacuo. The residue is taken up in chloroform. Sulfur is removed by filtration. The chloroform is evaporated in vacuo. The residue is distilled in vacuo to give 15.5 g (60% yield) of oily ethyl 1-methylpyrrole-2-acetate, b.p. 64°-66° C. at 0.06 Torr.

Workup

  1. custom2 hours
  2. additionThe reaction mixture is added dropwise
  3. customThe chloroform layer is separated
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo at room temperature

Sources & evidence

ORD record
ord-9c0cf985a05a4fc6a949c0a3e3dbc0b1
Source dataset
uspto-grants-1980_08
Patent number
US04216150

Reaction notes

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