Ammonia → 2-(2,2,2-Trifluoroethyl)guanidino-6-chloropyrazine

HRID 1902324Notes

Reaction equation

HRID 1902324 reaction equation
[F:1][C:2]([F:16])([F:15])[CH2:3][NH:4][C:5](=S)[NH:6][C:7]1[CH:12]=[N:11][CH:10]=[C:9]([Cl:13])[N:8]=1.[NH3:17]>>[F:1][C:2]([F:16])([F:15])[CH2:3][N:4]=[C:5]([NH2:17])[NH:6][C:7]1[CH:12]=[N:11][CH:10]=[C:9]([Cl:13])[N:8]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 544834192-Chloro-6-(3-[2,2,2-trifluoroethyl]thioureido)pyrazine

Product 1

HCID 212987082-(2,2,2-Trifluoroethyl)guanidino-6-chloropyrazine

Procedure

To a solution of 2-[3-(2,2,2-trifluoroethyl)-thioureido]-6-chloropyrazine (0.7 g.) in alcoholic ammonia (35 ml.) was added red mercuric oxide (0.65 g.) with stirring at room temperature. After stirring overnight, the black mixture was filtered and the black solid washed with alcohol. The resulting yellow filtrate was evaporated to give a yellow solid (0.7 g.). Recrystallisation from hot toluene diluted with petroleum ether (b.p. 60°-80°) yielded colourless needles (0.5 g.) of 2-[2-(2,2,2-trifluoroethyl)guanidino]-6-chloropyrazine m.p. 139°-140°.

Workup

  1. stirringAfter stirring overnight
  2. filtrationthe black mixture was filtered
  3. washthe black solid washed with alcohol
  4. customThe resulting yellow filtrate was evaporated
  5. customto give a yellow solid (0.7 g.)
  6. customRecrystallisation from hot toluene
  7. additiondiluted with petroleum ether (b.p. 60°-80°)

Sources & evidence

ORD record
ord-e5456f248dd943f6978b1483ad9dd10f
Source dataset
uspto-grants-1982_12
Patent number
US04362728

Reaction notes

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