p-Toluenesulfonic acid monohydrate → HCID 19704095, compound

HRID 861596Notes

Reaction equation

HRID 861596 reaction equation
CO[C:3](=[O:23])[CH:4]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[NH:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14]#[N:15])[N:13]=1)=[S:7].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:14]([C:12]1[N:13]=[C:9]([N:8]2[C:3](=[O:23])[CH:4]([CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:5][C:6]2=[S:7])[S:10][CH:11]=1)#[N:15]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 19703789HCID 19703789, compound

Product 1

HCID 19704095HCID 19704095, compoundYield 13.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of N-[[(4-cyano-2-thiazolyl)amino]thioxomethyl]-DL-phenylalanine methyl ester (1.42 g, 4.10 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 ether-hexanes to provide 170.1 mg (10%) 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 ether-hexanes

Sources & evidence

ORD record
ord-94b4559dfc514d97b28676a034ba4384
Source dataset
uspto-grants-1998_02
Patent number
US05714503

Reaction notes

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