Acetonitrile → p-Toluenesulfonic acid

HRID 217101Notes

Reaction equation

HRID 217101 reaction equation
C(#N)C.O.[C:5]1([CH3:15])[CH:10]=[CH:9][C:8]([S:11]([OH:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1>C(OC(C)C)(=O)C.C(O)C>[C:5]1([CH3:15])[CH:6]=[CH:7][C:8]([S:11]([OH:14])(=[O:12])=[O:13])=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 6342AcetonitrileHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 6101p-Toluenesulfonic acidYield 251.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 7915Isopropyl AcetateSolvent

Procedure

The filtrate from step (ii) that contains (5) dissolved in isopropyl acetate and acetonitrile is diluted with 5.5 L of 200 proof ethanol. While stirring, p-toluene sulfonic acid hydrate (1.04 kg, 5.49 mol) in 3.3 L of 200 proof ethanol is added dropwise over 30 minutes. An off white solid crystallizes from the reaction mixture. After stirring 16 hours the solid is collected by filtration, washed twice with 7.5 L portions of isopropyl acetate, and once with 3.5 L of 200 proof ethanol. The solid is dried in a vacuum oven to yield 2.38 kg of p-toluene sulfonic acid salt of 5-amino-3-(2′-O-acetyl-3′-deoxy-beta-D-ribofuranosyl)-3H-thiazolo[4,5]pyrimidine-2-one with >98% purity by HPLC.

Workup

  1. customAn off white solid crystallizes from the reaction mixture
  2. stirringAfter stirring 16 hours the solid
  3. filtrationis collected by filtration
  4. washwashed twice with 7.5 L portions of isopropyl acetate
  5. customThe solid is dried in a vacuum oven

Sources & evidence

ORD record
ord-c8fe9ed8127b45959d7e458d78ebb3c0
Source dataset
uspto-grants-2012_06
Patent number
US08193342B2

Reaction notes

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