Sulfuryl chloride → HCID 15010168, compound

HRID 1085602Notes

Reaction equation

HRID 1085602 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][CH:10]=[CH:11][C:12]=2[C:13]#[N:14])=[CH:4][CH:3]=1.S(Cl)([Cl:18])(=O)=O>C(O)(=O)C>[Cl:18][C:10]1[NH:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[C:12]([C:13]#[N:14])[CH:11]=1

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 146232102-(4-Chlorophenyl)-1H-pyrrole-3-carbonitrile

Product 1

HCID 15010168HCID 15010168, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a 35° C. magnetically stirred solution of 2.40 g (11.8 mmol., 1.00 equivalent) of 2-(p-chlorophenyl)pyrrole-3-carbonitrile, and 65 mL of glacial acetic acid is added dropwise by syringe 0.75 mL (1.26 g, 9.34 mmol., 0.79 equivalent) of sulfuryl chloride over a period of 5 minutes. Approximately 5 minutes after the completion of the addition, a solid precipitated out of the reaction solution. After stirring at room temperature for 45 minutes, the reaction mixture is filtered and the collected solid is washed well with cold acetic acid to give 2.08 g (74% crude yield) of an off-white solid. This solid is recrystallized from 75 mL of hot acetic acid to give 1.63 g (58% yield) of 97 wt % pure. Product mp 258.5°-261° C.

Workup

  1. additionApproximately 5 minutes after the completion of the addition
  2. customa solid precipitated out of the reaction solution
  3. filtrationthe reaction mixture is filtered
  4. washthe collected solid is washed well with cold acetic acid
  5. customto give 2.08 g (74% crude yield) of an off-white solid
  6. customThis solid is recrystallized from 75 mL of hot acetic acid
  7. customto give 1.63 g (58% yield) of 97 wt % pure

Sources & evidence

ORD record
ord-a5c43cef69144fd0ba296e21eb617a1f
Source dataset
uspto-grants-1991_04
Patent number
US05010098

Reaction notes

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