p-Toluenesulfonic acid monohydrate → HCID 10194040, compound

HRID 1268062Notes

Reaction equation

HRID 1268062 reaction equation
O[C:2]1([C:23]([F:26])([F:25])[F:24])[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]([CH:20]([CH3:22])[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:23]([F:26])([F:25])[F:24])[N:3]=[C:4]2[C:15]2[S:19][C:18]([CH:20]([CH3:22])[CH3:21])=[N:17][N:16]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 18543942HCID 18543942, compound

Product 1

HCID 10194040HCID 10194040, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-hydroxy-1-[4-(methylthio)phenyl]-2-[2-(isopropyl)-1,3,4-thiadiazol-5-yl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazole (0.361 g, 0.90 mmol) and p-toluenesulfonic acid monohydrate (35 mg) in toluene (50 mL) was heated to reflux for 1 hour. After aqueous work up, the product (0.26 g, 75%) was isolated as a white solid; 1H NMR δ (DMSO-d6) 8.37 (1H, s), 7.50 (2H, d, J=8.3 Hz), 7.38 (2H, d, J=8.6 Hz), 3.42 (1H, m), 2.55 (3H, s), 1.35 (6H, d, J=6.7 Hz); 13C NMR δ (DMSO-d6) 177.4, 157.6, 140.3, 138.5, 133.2, 130.9(q), 127.2, 126.4, 125.7, 122.5(q), 29.9, 22.7, 14.4.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour

Sources & evidence

ORD record
ord-47571f9bbae847d383450dbc9976283b
Source dataset
uspto-grants-2003_04
Patent number
US06555563B1

Reaction notes

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