Water → HCID 15087830, compound

HRID 1032477Notes

Reaction equation

HRID 1032477 reaction equation
C[C:2]([C:4]([C:14]([CH3:16])=[O:15])=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[Cl:13])=O.C1(C)C=CC(S([CH2:26][N+:27]#[C-])(=O)=O)=CC=1.C[O-].[Na+].O>CO>[CH3:16][C:14]([C:4]1[C:5]([C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=2[Cl:13])=[CH:26][NH:27][CH:2]=1)=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 161915Tosylmethyl isocyanideHCID 10942334Sodium MethoxideHCID 15087829HCID 15087829, compound

Product 1

HCID 15087830HCID 15087830, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

With stirring, 20 g of 1,1-di(methylcarbonyl)-2-(2,3-dichlorophenyl)ethene are added at 0° C. to 65 g of a 23.2% by weight solution of (p-tolylsulfonyl)methyl isocyanide prepared according to Example P1 (a). Then 28.1 g of a 30 % solution of sodium methylate in methanol are added dropwise over 3 hours. The mixture is stirred for 60 minutes at a temperature of +10° C. and then 170 ml of water are added dropwise and the product is subsequently isolated by filtration. The filter residue is recrystallised from a 1:1 mixture of methanol/ethanol and dried under vacuum, affording 8.3 g (50% of theory) of 4-methylcarbonyl-3-(2,3-dichlorophenyl)pyrrole which melts at 192°-194° C.

Workup

  1. customprepared
  2. stirringThe mixture is stirred for 60 minutes at a temperature of +10° C.
  3. customthe product is subsequently isolated by filtration
  4. customThe filter residue is recrystallised from a 1:1 mixture of methanol/ethanol
  5. customdried under vacuum

Sources & evidence

ORD record
ord-06c5fa3482e34a6a888ef31c73a2ce1e
Source dataset
uspto-grants-1990_09
Patent number
US04958030

Reaction notes

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