Chloroform → HCID 12897026, compound

HRID 894014Notes

Reaction equation

HRID 894014 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[CH:2]1.C(Cl)Cl.[C:13]1([CH3:21])[C:14]([S:19]Cl)=[CH:15][CH:16]=[CH:17][CH:18]=1.C(Cl)(Cl)Cl>CCOCC>[CH3:21][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19][C:5]1[NH:1][CH:2]=[C:3]([C:6]([O:8][CH3:9])=[O:7])[CH:4]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 6344DichloromethaneHCID 12361759methyl 1H-pyrrole-3-carboxylateHCID 12963243HCID 12963243, compound

Product 1

HCID 12897026HCID 12897026, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Under a nitrogen atmosphere, methyl pyrrole-3-carboxylate (2.5 g., 20 mmoles) was dissolved in 50 ml. of methylene chloride. The stirred solution was cooled in an ice-water bath and o-toluenesulfenyl chloride (3.16 g., 20 mmoles) was added dropwise. The reaction mixture was warmed to room temperature and stirred for 1 hour. Thin layer chromatography (silica gel, chloroform eluant) indicated virtually complete reaction at this time. An equal volume of ether was added and a small amount of insolubles removed by filtration. Crude product (5 g.) was obtained by evaporation in vacuo to a gum. The latter was chromatographed on 150 g. of silica gel with 75 ml. fractions of the chloroform eluant collected. Fractions 10 to 13 were combined and evaporated in vacuo to yield partially purified product (1.69 g., m.p. 114°-119° C.). Recrystallization from methylene chloride/hexane gave purified methyl 5-(2-methylphenylthio)pyrrole-3-carboxylate (1.1 g., m.p. 126°-128° C.).

Workup

  1. temperatureThe stirred solution was cooled in an ice-water bath
  2. customreaction at this time
  3. customa small amount of insolubles removed by filtration

Sources & evidence

ORD record
ord-34c46590dc3442c19b2a8a88849634c4
Source dataset
uspto-grants-1981_08
Patent number
US04282242

Reaction notes

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