p-Toluenesulfonic acid monohydrate → HCID 22923249, compound

HRID 2257781Notes

Reaction equation

HRID 2257781 reaction equation
CO[C:3](=[O:25])[CH:4]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[NH:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:13]=1)=[S:7].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:16][C:14]([F:15])([F:17])[C:12]1[N:13]=[C:9]([N:8]2[C:3](=[O:25])[CH:4]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[NH:5][C:6]2=[S:7])[S:10][CH:11]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 19704064HCID 19704064, compound

Product 1

HCID 22923249HCID 22923249, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of N-[[(4-trifluoromethyl-2-thiazolyl)amino]thioxomethyl]-DL-phenylalanine methyl ester (2.09 g, 5.38 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 48 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 1.01 g (53%) of the titled product: mp 187°-189° C.; IR (CHCl3, cm-1) 3431, 3008, 1782, 1495, 1369, 1328, 1242, 1178, 1149, 1085; 1H NMR (300 MHz, DMSO-d6) δ 11.02 (s, 1H), 8.59 (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 357 (M+); UV (EtOH) 263 nm (ε=13898), 202 nm (ε=19355). Anal. Calcd. for C14H10F3N3OS2 : C, 47.05; H,2.82; N,11.76. Found: C,47.33; H, 2.86; N, 11.67.

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-5126f0d36fd445e687e15ddbab284425
Source dataset
uspto-grants-1997_08
Patent number
US05658907

Reaction notes

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