Toluene → HCID 19931881, compound

HRID 21602Notes

Reaction equation

HRID 21602 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH3:5][C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH3:13])[C:7]=1[S:14]([C:17]1[CH:21]=[CH:20][NH:19][N:18]=1)(=[O:16])=[O:15].[C:22]1([CH3:28])[CH:27]=CC=CC=1>>[CH2:17]([N:18]([CH2:27][CH2:22][CH3:28])[C:1]([N:19]1[CH:20]=[CH:21][C:17]([S:14]([C:7]2[C:8]([CH3:13])=[CH:9][C:10]([CH3:12])=[CH:11][C:6]=2[CH3:5])(=[O:15])=[O:16])=[N:18]1)=[O:2])[CH2:21][CH3:20]

Participants

4

Reactant 3

HCID 1140Toluene2×HCID 6371PhosgeneHCID 178425951HCID 178425951, compound

Product 1

HCID 19931881HCID 19931881, compoundYield 89%

Conditions

Temperature
60 °C

Procedure

2 ml of a 1.98M solution of phosgene in toluene were added to a solution of 200 mg of 3-(2,4,6-trimethylphenylsulfonyl)pyrazole [prepared as described in step (2) above] in 1 ml of toluene, and the resulting solution was heated at 60° C. for 1 hour. The mixture was concentrated by evaporation under reduced pressure, and then 97 mg of triethylamine and 89 mg of diisopropylamine were added, in that order, to the oily residue. The reaction mixture was then stirred at ambient temperature for 20 minutes, after which it was diluted with diethyl ether. The ethereal solution was washed with 1N aqueous hydrochloric acid, with an aqueous solution of sodium hydrogencarbonate and with water, in that order, and was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, eluted with a 6:1 by volume mixture of hexane and ethyl acetate, to afford 268 mg (yield 89%) of the title compound, melting at 64°-65° C.

Workup

  1. concentrationThe mixture was concentrated by evaporation under reduced pressure
  2. addition97 mg of triethylamine and 89 mg of diisopropylamine were added, in that order, to the oily residue
  3. additionafter which it was diluted with diethyl ether
  4. washThe ethereal solution was washed with 1N aqueous hydrochloric acid, with an aqueous solution of sodium hydrogencarbonate and with water, in that order
  5. dry with materialwas then dried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. customthe resulting residue was purified by column chromatography through silica gel
  8. washeluted with a 6:1 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-b639f53386734c88b5484ad59f6b4a86
Source dataset
uspto-grants-1995_06
Patent number
US05424279

Reaction notes

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