Ammonia → 1-(2-Hydroxyethyl)-3-[2-(2,2,2-trifluoroethyl)guanidino]pyrazole

HRID 978406Notes

Reaction equation

HRID 978406 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([NH:12][CH2:13][C:14]([F:17])([F:16])[F:15])=S)=[N:5]1.[NH3:18]>CCO>[OH:1][CH2:2][CH2:3][N:4]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([NH2:18])=[N:12][CH2:13][C:14]([F:17])([F:16])[F:15])=[N:5]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 543739781-(2-Hydroxyethyl)-3-[3-(2,2,2-trifluoroethyl)thioureido]pyrazole

Product 1

HCID 212798481-(2-Hydroxyethyl)-3-[2-(2,2,2-trifluoroethyl)guanidino]pyrazoleYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-(2-hydroxyethyl)-3-[3-(2,2,2-trifluoroethyl)thioureido]pyrazole (20.0 g.) in 5N ammonia in EtOH solution (700 ml.) was added yellow mercuric oxide (64.8 g.) with stirring. Stirring was continued for a period of 2 hours. The mixture was filtered through diatomaceous earth and the solvent then evaporated to dryness in vacuo. The residual oil was triturated with ether to give 1-(2-hydroxyethyl)-3-[2-(2,2,2-trifluoroethyl)guanidino]pyrazole (18.5 g.; 99%), m.p. 82°.

Workup

  1. stirringStirring
  2. filtrationThe mixture was filtered through diatomaceous earth
  3. customthe solvent then evaporated to dryness in vacuo
  4. customThe residual oil was triturated with ether

Sources & evidence

ORD record
ord-5cc2962a239c4ff3a542d3606234f053
Source dataset
uspto-grants-1987_05
Patent number
US04665073

Reaction notes

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