Ethyl Acetate → p-Toluenesulfonic acid

HRID 2393777Notes

Reaction equation

HRID 2393777 reaction equation
C[C:2]1[CH:7]=[C:6]([S:8]([OH:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH3:12].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>C(O)=O>[CH3:12][C:3]1[CH:2]=[CH:7][C:6]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8857Ethyl Acetate2×HCID 147563,4-Dimethylbenzene-1-sulfonic acidHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 6101p-Toluenesulfonic acidYield 53%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

1H-2-[1-Methyl-4-(3-methylthiopropionyl)aminopyrrol-2-yl]benzimidazole-5-[N-[4-[N,N-bis(2-chloroethyl)amino]phenyl]]carboxamide (10.1 g) was dissolved in 35 ml of 98-100% formic acid. To this solution were added 8 ml of methyl p-toluenesulfonic acid and 4.1 g (1.2 equivalents) of p-toluenesulfonic acid monohydrate, and then the mixture was stirred at room temperature for 2 days in darkness. Treatment with ethyl acetate and decantation were repeated 2 times each (700 ml×2), and then sludging was carried out with 300 ml of ethyl acetate to obtain a light yellow powder. This was purified by chromatography on a gel filtration column (Sephadex LH-20, methanol) and was recrystallized from methanol, whereby 8.72 g (53%) of the title compound were obtained.

Workup

  1. customto obtain a light yellow powder
  2. filtrationThis was purified by chromatography on a gel filtration column (Sephadex LH-20, methanol)
  3. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-bc3cc87a0dd4441499b8b71b84cf7afe
Source dataset
uspto-grants-1998_09
Patent number
US05808087

Reaction notes

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