Dimethylformamide → HCID 18930425, compound

HRID 1975220Notes

Reaction equation

HRID 1975220 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])=[CH:11][N:10]([CH3:20])[CH:9]=2)=[CH:4][CH:3]=1.[Cl:21]S(N=C=O)(=O)=O.CN(C)C=O>C(COC)OC.O>[Cl:21][C:9]1[N:10]([CH3:20])[CH:11]=[C:12]([S:13]([C:16]([F:17])([F:19])[F:18])(=[O:14])=[O:15])[C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 70918Chlorosulfonyl isocyanate2×HCID 18930421HCID 18930421, compound

Product 1

HCID 18930425HCID 18930425, compoundYield 37.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 3-(p-chlorophenyl)-1-methyl-4-[(trifluoromethyl)sulfonyl]pyrrole (0.5 g, 0.0015 mol) in dimethoxyethane is treated with chlorosulfonyl isocyanate (0.3 mL, 0.0034 mol), stirred for 24 hours at room temperature, treated with additional chlorosulfonyl isocyanate (0.6 mL, 0.0068 mol), stirred for 24 hours, treated with dimethylformamide (2 mL), stirred for one hour, diluted with water and extracted with ether. The combined organic extracts are washed with water, dried and concentrated in vacuo to obtain a semi-solid. Flash chromatography of the semi-solid using silica gel and a 1:4 ethyl acetate/hexanes solution gives the title product as a white solid (0.2 g, mp 117°-119° C.) which is identified by 1HNMR and 13CNMR spectral analyses.

Workup

  1. stirringstirred for 24 hours
  2. stirringstirred for one hour
  3. extractionextracted with ether
  4. washThe combined organic extracts are washed with water
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customto obtain a semi-solid

Sources & evidence

ORD record
ord-6d0375c8c4a840288e43b8fbe1278faa
Source dataset
uspto-grants-1994_02
Patent number
US05284863

Reaction notes

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