Hydrochloric Acid → HCID 19965976, compound

HRID 1734894Notes

Reaction equation

HRID 1734894 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12](S(C2C=CC(C)=CC=2)(=O)=O)(SC)[CH2:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:7][C:6]=1[N+:32]([O-:34])=[O:33])([CH3:4])([CH3:3])[CH3:2].Cl.C[OH:37]>>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12](=[O:37])[CH2:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:7][C:6]=1[N+:32]([O-:34])=[O:33])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 19966065HCID 19966065, compound

Product 1

HCID 19965976HCID 19965976, compoundYield 73%

Procedure

The whole of the 2-t-butyl-5-[3-cyclohexyl-2-(4-methylphenyl)sulfonyl-2-methylthiopropyl]-1-nitrobenzene prepared as described in step (i) above was dissolved in 50 ml of methanol. 5 ml of concentrated aqueous hydrochloric acid were added, and the resulting solution was heated for 2 hours under reflux. At the end of this time, the solvent was removed by distillation under reduced pressure. The resulting residue was dissolved in diethyl ether, and the solution was washed with water, with a saturated aqueous solution of sodium hydrogen carbonate, with water and with a saturated aqueous solution of sodium chloride, in that order. The solvent was then removed by distillation under reduced pressure. The resulting residue was subjected to column chromatography through 150 g of silica gel. Elution with a 1:5 by volume mixture of ethyl acetate and hexane afforded 1.20 g (yield 73%) of the title compound as an oily substance.

Workup

  1. temperaturethe resulting solution was heated for 2 hours
  2. temperatureunder reflux
  3. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  4. dissolutionThe resulting residue was dissolved in diethyl ether
  5. washthe solution was washed with water, with a saturated aqueous solution of sodium hydrogen carbonate, with water and with a saturated aqueous solution of sodium chloride, in that order
  6. customThe solvent was then removed by distillation under reduced pressure
  7. washElution with a 1:5
  8. additionby volume mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-eb2b393f1153400cb8739895bc7c12dc
Source dataset
uspto-grants-1996_07
Patent number
US05534529

Reaction notes

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