Acetonitrile → HCID 178512202, compound

HRID 1463059Notes

Reaction equation

HRID 1463059 reaction equation
[F:1][C:2]([F:8])([F:7])[CH2:3][N:4]=[C:5]=S.[NH2:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]2[N:21]=[CH:22][NH:23][CH:24]=2)[N:11]=1.C(#[N:27])C>>[F:1][C:2]([F:8])([F:7])[CH2:3][N:4]=[C:5]([NH2:27])[NH:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]2[N:21]=[CH:22][NH:23][CH:24]=2)[N:11]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 138837771,1,1-Trifluoro-2-isothiocyanatoethaneHCID 178507898HCID 178507898, compound

Product 1

HCID 178512202HCID 178512202, compound

Procedure

A mixture of (2,2,2-trifluoroethyl)isothiocyanate (0.43 g.) and 4-(4-[4-aminopyrimid-2-yl]butyl)imidazole (0.35 g.) was heated under reflux in acetonitrile for 18 hours. It was then evaporated to dryness and the residue purified by medium pressure liquid chromatography using a mixture of CHCl3 /MeOH/aqueous ammonia (s.g. 0.880) 15:1:0.05 v/v/v) as eluant. The appropriate fraction was evaporated to dryness and the residue of the thiourea was dissolved in concentrated ethanolic ammonia (15 ml.) and mercuric oxide (0.2 g.) added. The resulting mixture was stirred at room temperature for 30 minutes, filtered and the filtrate evaporated to dryness. The residue was dissolved in EtOH (10 ml.), treated with a small amount of hydrogen sulphide gas, filtered and the filtrate evaporated to dryness. The residue was crystallised from acetonitrile to give 4-[4-(4-[2-(2,2,2-trifluoroethyl)guanidino]pyrimid-2-yl)butyl]imidazole (0.075 g.), m.p. 191°-193°.

Workup

  1. temperaturewas heated
  2. customIt was then evaporated to dryness
  3. customthe residue purified by medium pressure liquid chromatography
  4. additiona mixture of CHCl3 /MeOH/aqueous ammonia (s.g. 0.880) 15:1:0.05 v/v/v) as eluant
  5. customThe appropriate fraction was evaporated to dryness
  6. dissolutionthe residue of the thiourea was dissolved in concentrated ethanolic ammonia (15 ml.)
  7. additionmercuric oxide (0.2 g.) added
  8. filtrationfiltered
  9. customthe filtrate evaporated to dryness
  10. dissolutionThe residue was dissolved in EtOH (10 ml.)
  11. additiontreated with a small amount of hydrogen sulphide gas
  12. filtrationfiltered
  13. customthe filtrate evaporated to dryness
  14. customThe residue was crystallised from acetonitrile

Sources & evidence

ORD record
ord-6271899bba954a17a1e6a8594b279fb1
Source dataset
uspto-grants-1984_07
Patent number
US04463005

Reaction notes

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