p-Toluenesulfonic acid monohydrate → HCID 19704188, compound

HRID 2257779Notes

Reaction equation

HRID 2257779 reaction equation
CO[C:3](=[O:26])[CH:4]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH:5][C:6]([NH:8][C:9]1[S:10][C:11]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:12]=2[N:13]=1)=[S:7].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:18][C:16]1[CH:15]=[CH:14][C:12]2[N:13]=[C:9]([N:8]3[C:3](=[O:26])[CH:4]([CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[NH:5][C:6]3=[S:7])[S:10][C:11]=2[CH:17]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 19703555HCID 19703555, compound

Product 1

HCID 19704188HCID 19704188, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of N-[[(6-fluoro-2-benzothiazolyl)amino]thioxomethyl]-DL-phenylalanine methyl ester (0.90 g, 2.31 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 251 mg (31%) of the titled product: mp 223°-224° C.; IR (KBr, cm-1) 3173, 1767, 1538, 1453, 1388, 1267; 1H NMR (300 MHZ, DMSO-d6) δ 11.02 (s, 1H), 8.00-8.12 (m, 2H), 7.40-7.50 (m, 1H), 7.20-7.39 (m, 5H), 4.97 (t, 1H), 3.20 (d, 2H); MS (FD) m/e 357(M+); UV (EtOH) 265 nm (ε=15680), 223 nm (ε=19505), 201 nm (ε=23665). Anal. Calcd for C17H12FN3OS2 : C, 57.13; H,3.38; N,11.76. Found: C,56.89; H, 3.43; N, 11.60.

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-ffbf2c6b079d48ea815b20e1429ef706
Source dataset
uspto-grants-1997_08
Patent number
US05658907

Reaction notes

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