1,1,1-Trifluoro-2-isothiocyanatoethane → 1-(2-Hydroxyethyl)-3-[3-(2,2,2-trifluoroethyl)thioureido]pyrazole

HRID 2291330Notes

Reaction equation

HRID 2291330 reaction equation
[F:1][C:2]([F:8])([F:7])[CH2:3][N:4]=[C:5]=[S:6].[NH2:9][C:10]1[CH:14]=[CH:13][N:12]([CH2:15][CH2:16][OH:17])[N:11]=1>C(#N)C>[OH:17][CH2:16][CH2:15][N:12]1[CH:13]=[CH:14][C:10]([NH:9][C:5]([NH:4][CH2:3][C:2]([F:8])([F:7])[F:1])=[S:6])=[N:11]1

Participants

4

Reactant 2

HCID 138837771,1,1-Trifluoro-2-isothiocyanatoethaneHCID 212798532-(3-Amino-1H-pyrazol-1-yl)ethan-1-ol

Product 1

HCID 543739781-(2-Hydroxyethyl)-3-[3-(2,2,2-trifluoroethyl)thioureido]pyrazoleYield 46.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2,2,2-trifluoroethylisothiocyanate (13.8 g.) and 3-amino-1-(2-hydroxyethyl)pyrazole (12.5 g.) in acetonitrile dried over 4A molecular sieve (30 ml.) was stirred at room temperature for 4 hours. A precipitate formed after 30 minutes. Filtration gave 1-(2-hydroxyethyl)-3-[3-(2,2,2-trifluoroethyl)thioureido]pyrazole (12.1 g.; 46%), m.p. 145°-146°.

Workup

  1. dry with materialdried over 4A molecular sieve (30 ml.)
  2. customA precipitate formed after 30 minutes
  3. filtrationFiltration

Sources & evidence

ORD record
ord-13ce0ae1ea97457cb53735bdae982281
Source dataset
uspto-grants-1989_01
Patent number
US04795755

Reaction notes

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