Acetonitrile → p-Toluenesulfonic acid

HRID 2076768Notes

Reaction equation

HRID 2076768 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-6063b4c8c98d412290c8fe4b3946654d
Source dataset
uspto-grants-2011_04
Patent number
US07928085B2

Reaction notes

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