p-Toluenesulfonic acid → 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-3-(2-methylthiazolidine-2-yl)-4-methylsulfinyl-1H-pyrazole

HRID 1106688Notes

Reaction equation

HRID 1106688 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19](=O)[CH3:20])[C:3]=1[S:22]([CH3:24])=[O:23].Cl.[NH2:26][CH2:27][CH2:28][SH:29].C(N(CC)CC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>O.C1C=CC=CC=1>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]2([CH3:20])[NH:26][CH2:27][CH2:28][S:29]2)[C:3]=1[S:22]([CH3:24])=[O:23]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 9082Cysteamine HydrochlorideHCID 11069398Acetoprole

Product 1

HCID 224611975-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-3-(2-methylthiazolidine-2-yl)-4-methylsulfinyl-1H-pyrazoleYield 1.7%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A mixture of 1 g (2.5 mmol) of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-3-acetyl-4-methylsulfinyl-1H-pyrazole, 0.284 g (2.5 mmol) of 2-aminoethanethiol hydrochloride, 348 microliters (2.50 mmol) of triethylamine, 50 mg of p-toluenesulfonic acid and 30 ml of benzene was heated to reflux with removal of water overnight. The mixture was successively cooled, filtered, evaporated, chromatographed so as to give 20 mg of the title compound as white solid; melting point 85° C.

Workup

  1. temperaturewas heated
  2. temperatureThe mixture was successively cooled
  3. filtrationfiltered
  4. customevaporated
  5. customchromatographed so as

Sources & evidence

ORD record
ord-5cf8d0d23a09454ba9992e2d6f70a9b4
Source dataset
uspto-grants-2000_05
Patent number
US06057354

Reaction notes

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