p-Toluenesulfonic acid → HCID 15158828, compound

HRID 1087120Notes

Reaction equation

HRID 1087120 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][NH: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.[OH-].[Ca+2].[OH-]>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][NH:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]#[N:13])=[CH:14][CH:15]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 15158827HCID 15158827, compound

Product 1

HCID 15158828HCID 15158828, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-10 °C

Procedure

A solution of 4-[[3-[ethyl[3-(propylthio)propyl]amino]-2-hydroxy-propyl]amino]-benzonitrile (2.0 g, 5.9 mmol) and toluene-4-sulfonic acid (2.3 g, 11.9 mmol) in ethanol (50 ml) was stirred 1/2 h at room temperature. The mixture was cooled to -10 ° C. and solid 3-chloroperbenzoic acid was added during 1/2 h. The solution was stirred for 1 h at room temperature. Solid calcium hydroxide (1.2 g, 16.4 mmol) was added, followed by stirring for 15 minutes. Filtration and evaporation gave an oily residue. Purification by column chromatography on silica gel yielded 1.0 g of the title compound.

Workup

  1. stirringby stirring for 15 minutes
  2. filtrationFiltration and evaporation
  3. customgave an oily residue
  4. customPurification by column chromatography on silica gel

Sources & evidence

ORD record
ord-b9aea8e300ca41629e885abb3716bbaa
Source dataset
uspto-grants-1991_07
Patent number
US05034411

Reaction notes

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