Water → HCID 23347805, compound

HRID 1855723Notes

Reaction equation

HRID 1855723 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=O)[C:8]([O:10][CH2:11][CH3:12])=[O:9].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[C:15]1([N:14]=[C:7]([C:3]2[N:2]([CH3:1])[CH:6]=[CH:5][CH:4]=2)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 6115AnilineHCID 89094Ethyl 1-methyl-alpha-oxo-1H-pyrrole-2-acetate

Product 1

HCID 23347805HCID 23347805, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4.0 g ethyl 1-methylpyrrole-2-glyoxylate and 2.23 g aniline in 20 ml toluene is added 30 mg p-toluenesulfonic acid. Heating at reflux for 2 days with water being removed with a Dean-Stark trap is followed by dilution with ether. The precipitate is removed by filtration and the filtrate washed successively with aqueous hydrochloric acid, aqueous sodium bicarbonate and brine. After drying, the solvent is evaporated to afford a residue which is recrystallized twice from isopropanol to give a 43% yield of ethyl α-phenylimino-1-methylpyrrole-2-acetate, m.p. 69°-71° C.

Workup

  1. temperatureHeating
  2. customremoved with a Dean-Stark trap
  3. customThe precipitate is removed by filtration
  4. washthe filtrate washed successively with aqueous hydrochloric acid, aqueous sodium bicarbonate and brine
  5. customAfter drying
  6. customthe solvent is evaporated
  7. customto afford a residue which
  8. customis recrystallized twice from isopropanol

Sources & evidence

ORD record
ord-15265e25eb14482882cc96a8fd592311
Source dataset
uspto-grants-1980_08
Patent number
US04216150

Reaction notes

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