Sulfuryl chloride → HCID 19759351, compound

HRID 248387Notes

Reaction equation

HRID 248387 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]([CH3:17])=[CH:15][CH:14]=[C:13]2[C:18]#[N:19])=[CH:8][CH:7]=1)=[O:5])[CH3:2].S(Cl)([Cl:23])(=O)=O>ClC(Cl)(Cl)Cl>[Cl:23][C:15]1[CH:14]=[C:13]([C:18]#[N:19])[N:12]([C:9]2[CH:10]=[CH:11][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:7][CH:8]=2)[C:16]=1[CH3:17]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 19759338HCID 19759338, compound

Product 1

HCID 19759351HCID 19759351, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
5 °C

Procedure

To a suspension of 1-(4-ethoxycarbonylphenyl)-5-methylpyrrole-2-carbonitrile (1.76 g) and silica gel (8.0 g, Mallinckrodt) in tetrachloromethane (26 ml) was added dropwise sulfuryl chloride (760 μl) at 5° C. under nitrogen atmosphere. The suspension was stirred at 5° C. for one hour and then at ambient temperature for half an hour. The mixture was filtered off and washed with a little amount of tetrachloromethane. The filtrate was concentrated in vacuo and the residue was purified by column chromatography on silica gel (elution by ethyl acetate/n-hexane=1/7) to yield 4-chloro-1-(4-ethoxycarbonylphenyl)-5-methylpyrrole-2-carbonitrile (1.36 g).

Workup

  1. waitat ambient temperature for half an hour
  2. filtrationThe mixture was filtered off
  3. washwashed with a little amount of tetrachloromethane
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by column chromatography on silica gel (elution by ethyl acetate/n-hexane=1/7)

Sources & evidence

ORD record
ord-9d5b3914b40e47b4ba87a08b95c120e4
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Reaction notes

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