2-Amino-6-Chloropyrazine → 2-Chloro-6-(3-[2,2,2-trifluoroethyl]thioureido)pyrazine

HRID 1902323Notes

Reaction equation

HRID 1902323 reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[F:9][C:10]([F:16])([F:15])[CH2:11][N:12]=[C:13]=[S:14]>C(#N)C>[F:9][C:10]([F:16])([F:15])[CH2:11][NH:12][C:13](=[S:14])[NH:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1

Participants

4

Reactant 2

HCID 1184582-Amino-6-ChloropyrazineHCID 138837771,1,1-Trifluoro-2-isothiocyanatoethane2×

Product 1

HCID 544834192-Chloro-6-(3-[2,2,2-trifluoroethyl]thioureido)pyrazineYield 36.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-amino-6-chloropyrazine (1 g.) in warm acetonitrile (15 ml.) was cooled to room temperature. Trifluoroethylisothiocyanate (1.6 g.) was added and the mixture stirred overnight. Further trifluoroethylisothiocyanate (1.6 g.) was added, and the mixture warmed gently on a steam bath for 2 hours, then heated under reflux for 2 hours. The mixture was allowed to cool and evaporated to dryness to yield a brown solid. This was washed with water, 2 N HCl solution, water again, and sucked dry. Recrystallisation from boiling toluene diluted with petroleum ether (b.p. 60°-80°) yielded colourless needles (0.77 g.) of 2-[3-(2,2,2-trifluoroethyl)thioureido]-6-chloropyrazine m.p. 170°-172°.

Workup

  1. temperaturethe mixture warmed gently on a steam bath for 2 hours
  2. temperatureheated
  3. temperatureunder reflux for 2 hours
  4. temperatureto cool
  5. customevaporated to dryness
  6. customto yield a brown solid
  7. washThis was washed with water, 2 N HCl solution, water again
  8. customsucked dry
  9. customRecrystallisation
  10. additiondiluted with petroleum ether (b.p. 60°-80°)

Sources & evidence

ORD record
ord-4d7a98316825454794b3ad8e64ccea7a
Source dataset
uspto-grants-1982_12
Patent number
US04362728

Reaction notes

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