Water → HCID 22494742, compound

HRID 1816705Notes

Reaction equation

HRID 1816705 reaction equation
CS(O[CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)(=O)=O.[C:21]([O-:24])(=[S:23])[CH3:22].[K+].O>CS(C)=O>[C:21]([S:23][CH:6]1[CH2:7][CH2:8][N:9]([C:12]2[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=2)[CH2:10][CH2:11]1)(=[O:24])[CH3:22]

Participants

5

Reactant 3

HCID 962WaterHCID 22494745HCID 22494745, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 22494742HCID 22494742, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 4-[4-(methanesulfonyloxy)piperidin-1-yl]nitrobenzene (2.0 g), and potassium thioacetate (1.14 g) in dimethylsulfoxide (DMSO) (20 ml) was stirred at 100-110° C. for 3 hours. The reaction mixture was poured into water (100 ml) and extracted twice with ethyl acetate (100 ml). The extracts were collected, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo. The resulting precipitates were washed with IPE (50 ml), collected by filtration and dried in vacuo to give 4-(4-acetylthiopiperidin-1-yl)nitrobenzene (1.15 g).

Workup

  1. extractionextracted twice with ethyl acetate (100 ml)
  2. customThe extracts were collected
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo
  6. customThe resulting precipitates
  7. washwere washed with IPE (50 ml)
  8. filtrationcollected by filtration
  9. customdried in vacuo

Sources & evidence

ORD record
ord-d498a9bf76d6455d91d93ababd0d176a
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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