p-Toluenesulfonic acid → Almokalant

HRID 974191Notes

Reaction equation

HRID 974191 reaction equation
[CH2:1]([N:3]([CH2:17][CH2:18][CH2:19][S:20][CH2:21][CH2:22][CH3:23])[CH2:4][CH:5]([OH:16])[CH2:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1)[CH3:2].C1(C)C=CC(S(O)(=O)=[O:31])=CC=1.ClC1C=CC=C(C(OO)=O)C=1>C(O)C>[CH2:1]([N:3]([CH2:17][CH2:18][CH2:19][S:20]([CH2:21][CH2:22][CH3:23])=[O:31])[CH2:4][CH:5]([OH:16])[CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]#[N:13])=[CH:14][CH:15]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 70297m-Chloroperbenzoic acidHCID 150668434-(3-{Ethyl[3-(propylsulfanyl)propyl]amino}-2-hydroxypropoxy)benzonitrile

Product 1

HCID 3033962Almokalant

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-10 °C

Procedure

2.45 g of 4-[3-[ethyl[3-(propylthio)propyl]amino]-2-hydroxypropoxy]-benzonitrile and 1.4 g p-toluenesulfonic acid were mixed in 50 ml of ethanol. The mixture was cooled to -10° C. and 1.7 g of m-chloroperbenzoic acid was added in small protions. The mixture was stirred for 0.5 hour at -10° C. and one hour at room temperature and then evaporated. The residue was dissolved in dichloromethane and washed with three portions of sodium carbonate and twice with water and thereafter dried over sodium sulfate, filtrated and evaporated. The residue, 2.3 g yellow oil, was purified by column chromatography. Yield: 1.4 g of the title compound.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with three portions of sodium carbonate and twice with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltrated
  6. customevaporated
  7. customThe residue, 2.3 g yellow oil, was purified by column chromatography

Sources & evidence

ORD record
ord-68d18174b05b400685f6a6fb7df98a6c
Source dataset
uspto-grants-1991_11
Patent number
US05068272

Reaction notes

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