Dimethylformamide → HCID 67786069, compound

HRID 129650Notes

Reaction equation

HRID 129650 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2C=CN(C)[C:9]=2[S:14]([C:17]([F:20])([F:19])[F:18])(=[O:16])=[O:15])=[CH:4][CH:3]=1.[Cl:21]S(N=C=O)(=O)=O.[CH3:28][N:29]([CH3:32])[CH:30]=O>C(COC)OC.O>[Cl:21][C:8]1([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:9]([S:14]([C:17]([F:20])([F:19])[F:18])(=[O:16])=[O:15])=[CH:30][N:29]([CH3:32])[CH2:28]1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 70918Chlorosulfonyl isocyanate2×HCID 19371959HCID 19371959, compound

Product 1

HCID 67786069HCID 67786069, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 3-(p-chlorophenyl)-1-methyl-[(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-b458da581bc24f7084d73c25e7d537f2
Source dataset
uspto-grants-1995_11
Patent number
US05468877

Reaction notes

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