p-Toluenesulfonic acid monohydrate → HCID 18543918, compound

HRID 1268061Notes

Reaction equation

HRID 1268061 reaction equation
O[C:2]1([C:22]([F:25])([F:24])[F:23])[CH2:6][N:5]([C:7]2[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=2)[C:4]([C:15]2[S:19][C:18]([S:20][CH3:21])=[N:17][N:16]=2)=[N:3]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:14][S:13][C:10]1[CH:11]=[CH:12][C:7]([N:5]2[CH:6]=[C:2]([C:22]([F:25])([F:24])[F:23])[N:3]=[C:4]2[C:15]2[S:19][C:18]([S:20][CH3:21])=[N:17][N:16]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 12045058HCID 12045058, compound

Product 1

HCID 18543918HCID 18543918, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-hydroxy-1-[4-(methylthio)phenyl]-2-[2-(methylthio)-1,3,4-thiadiazol-5-yl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazole (0.52 g, 1.28 mmol) and p-toluenesulfonic acid monohydrate (0.1 g) in toluene (20 mL) was heated to reflux for 1 hour. The reaction mixture was cooled to room temperature and the solvent was removed in vacuo. The crude residue was redissolved in ethyl acetate and washed with water, aqueous sodium bicarbonate and brine. After drying (Na2SO4), filtration, and concentration in vacuo, the crude mixture was purified by chromatography on silica gel using hexane/ethyl acetate to give the title product (0.4 g, 80%) as a white solid; 1H NMR δ (DMSO-d6) 8.38 (1H, s), 7.51 (2H, d, J=8.7 Hz), 7.38 (2H, d, J=8.3 Hz), 2.76 (3H, s), 2.55 (3H, s); 13C NMR δ (DMSO-d6) 168.8, 157.4, 140.4, 138.0, 133.0, 131.0(q), 127.2, 126.4, 125.7, 122.0(q), 16.4, 14.4.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour
  3. customthe solvent was removed in vacuo
  4. dissolutionThe crude residue was redissolved in ethyl acetate
  5. washwashed with water, aqueous sodium bicarbonate and brine
  6. customAfter drying
  7. filtration(Na2SO4), filtration, and concentration in vacuo
  8. customthe crude mixture was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-e3230cc3c65b49ccb4b2a9eb70443ed0
Source dataset
uspto-grants-2003_04
Patent number
US06555563B1

Reaction notes

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