Acetonitrile → p-Toluenesulfonic acid

HRID 217099Notes

Reaction equation

HRID 217099 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 212.5%

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 100 mL of 200 proof ethanol. While stirring, p-toluene sulfonic acid hydrate (15.89 g, 83.49 mmol) in 50 mL 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 100 mL portions of isopropyl acetate, and once with 50 mL of 200 proof ethanol. The solid is dried in a vacuum oven to yield 30.55 g of p-toluene sulfonic acid salt of 5-amino-3-(2′-O-acetyl-3′-deoxy-β-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 100 mL portions of isopropyl acetate
  5. customThe solid is dried in a vacuum oven

Sources & evidence

ORD record
ord-e8b5d527ff434b0c822a5ff2771191cf
Source dataset
uspto-grants-2012_06
Patent number
US08193342B2

Reaction notes

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