p-Toluenesulfonic acid monohydrate → HCID 19703971, compound

HRID 233696Notes

Reaction equation

HRID 233696 reaction equation
CO[C:3](=[O:22])[CH:4]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[NH:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([CH3:14])[N:13]=1)=[S:7].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:14][C:12]1[N:13]=[C:9]([N:8]2[C:3](=[O:22])[CH:4]([CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:5][C:6]2=[S:7])[S:10][CH:11]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 19703951HCID 19703951, compound

Product 1

HCID 19703971HCID 19703971, compoundYield 25.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of N-[[(4-methyl-2-thiazolyl)amino]thioxomethyl]-DL-phenylalanine methyl ester (0.94 g, 2.80 mmol) and p-toluene sulfonic acid hydrate (0.20 g 1.05 mmol) in toluene (80 mL) was refluxed with a Dean-Stark trap for 24 h. The reaction was cooled to room temperature, solvent removed under reduced pressure, residue taken up in ethyl acetate, washed with saturated sodium bicarbonate and saturated sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting product was recrystallized from ethyl acetate-hexanes to provide 216.1 mg (25%) of the titled product:

Workup

  1. customsolvent removed under reduced pressure, residue
  2. washwashed with saturated sodium bicarbonate and saturated sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting product was recrystallized from ethyl acetate-hexanes

Sources & evidence

ORD record
ord-12dd83a6ba934ceda1959a9e608cfe88
Source dataset
uspto-grants-1997_01
Patent number
US05593993

Reaction notes

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