Water → Methyl 4-(2,3-dichlorophenyl)-1H-pyrrole-3-carboxylate

HRID 1032478Notes

Reaction equation

HRID 1032478 reaction equation
C[C:2]([C:4](=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:11]=1[Cl:17])[C:5]([O:7][CH3:8])=[O:6])=O.C1(C)C=CC(S([CH2:27][N+:28]#[C-])(=O)=O)=CC=1.C[O-].[Na+].O>CO>[CH3:8][O:7][C:5]([C:4]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:11]=2[Cl:17])=[CH:27][NH:28][CH:2]=1)=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 161915Tosylmethyl isocyanideHCID 10942334Sodium MethoxideHCID 54242386Butanoic acid, 2-[(2,3-dichlorophenyl)methylene]-3-oxo-, methyl ester

Product 1

HCID 15087831Methyl 4-(2,3-dichlorophenyl)-1H-pyrrole-3-carboxylateYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

With stirring, 20 g of methyl α-methylcarbonyl-2,3-dichlorocinnamate are added at 0° C. to a 22 % by weight solution of (p-tolylsulfonyl)methyl isocyanide prepared according to Example P1 (a). Then 26.3 g of a 30% solution of sodium methylate in methanol are added dropwise over 2 hours. The mixture is stirred for 2 hours and then 35 ml of water are added dropwise. The reaction mixture is concentrated at +50° C. under vacuum. After addition of 70 ml of water, the reaction mixture is concentrated once more under vacuum and then filtered. The filter residue is washed with toluene and recrystallised from ethanol, affording 10.8 g (58% of theory) of 4-methoxycarbonyl-3-(2,3-dichlorophenyl)-pyrrole which melts at 200°-201° C.

Workup

  1. customprepared
  2. stirringThe mixture is stirred for 2 hours
  3. concentrationThe reaction mixture is concentrated at +50° C. under vacuum
  4. additionAfter addition of 70 ml of water
  5. concentrationthe reaction mixture is concentrated once more under vacuum
  6. filtrationfiltered
  7. washThe filter residue is washed with toluene
  8. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-d5b83b86c40c4ba0a9b467df0b383263
Source dataset
uspto-grants-1990_09
Patent number
US04958030

Reaction notes

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