p-Toluenesulfonic acid monohydrate → HCID 19704095, compound

HRID 2257780Notes

Reaction equation

HRID 2257780 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: mp 214°-216° C.; IR (KBr, cm-1) 3294, 3092, 2246, 1781, 1505, 1381, 1325, 1244; 1H NMR (300 MHz, DMSO-d6) δ 11.08 (s, 1H), 8.90 (s, 1H), 7.22-7.80 (m, 3H), 7.20-7.22 (m, 2H), 4.83 (t, 1H), 3.17 (d, 2H); MS (FD) m/e 314(M+); UV (EtOH) 259 nm (ε=15097), 205 nm (ε=26419). Anal. Calcd for C14H10N4OS2 : C, 53.49; H, 3.21; N,17.82. Found: C, 53.75; H, 3.43; N, 17.62.

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-a812d1bbb87848b684334cd4e591144d
Source dataset
uspto-grants-1997_08
Patent number
US05658907

Reaction notes

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