Dimethylformamide → HCID 178485208, Verbindung

HRID 1902283

Reaktionsgleichung

Reaktionsgleichung von HRID 1902283
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]([NH:21][CH3:22])=[N:16][S:17]([CH3:20])(=[O:19])=[O:18])[N:3]=1.[F:23][C:24]([F:30])([F:29])[CH2:25][N:26]=[C:27]=S.C[N:32](C)C=O>>[NH2:8][C:6]1[N:7]=[C:2]([NH:1][C:27]([NH2:32])=[N:26][CH2:25][C:24]([F:30])([F:29])[F:23])[N:3]=[C:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]([NH:21][CH3:22])=[N:16][S:17]([CH3:20])(=[O:19])=[O:18])[N:5]=1

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 138837771,1,1-Trifluoro-2-isothiocyanatoethaneHCID 178485209HCID 178485209, Verbindung

Produkt 1

HCID 178485208HCID 178485208, Verbindung

Versuchsvorschrift

A mixture of 2,4-diamino-6-[5-(2-methanesulphonyl-3-methylguanidino)pentyl]-1,3,5-triazine (0.4 g.), 2,2,2-trifluoroethylisothiocyanate (0.4 g.) and dimethylformamide (0.5 ml.) was heated at 120° for 1 hour and then at 60° for 18 hours. The mixture was evaporated to dryness, the residue partitioned between water and ethyl acetate, and the ethyl phase was separated, dried, and evaporated to dryness. The residue was dissolved in saturated ethanolic ammonia (10 ml.) and the solution treated with yellow mercuric oxide (0.5 g.). The mixture was stirred at room temperature for 18 hours, filtered and the filtrate evaporated to dryness. The residue was purified by chromatography using ethyl acetate/methanol/ammonia 6:1:0.5 v/v/v as developing solvent to give 2-amino-4-[2-(2,2,2-trifluoroethyl)-guanidino]-6-[5-(2-methanesulphonyl-3-methylguanidino)-pentyl]-1,3,5-triazine (0.07 g.) characterised as the bishydrogen maleate, m.p. 131°-133° after recrystallisation from acetone.

Aufarbeitung

  1. temperaturewas heated at 120° for 1 hour
  2. customThe mixture was evaporated to dryness
  3. customthe residue partitioned between water and ethyl acetate
  4. customthe ethyl phase was separated
  5. customdried
  6. customevaporated to dryness
  7. dissolutionThe residue was dissolved in saturated ethanolic ammonia (10 ml.)
  8. additionthe solution treated with yellow mercuric oxide (0.5 g.)
  9. filtrationfiltered
  10. customthe filtrate evaporated to dryness
  11. customThe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6a86230cfd6a46768c0ed3d3b8348662
Quelldatensatz
uspto-grants-1982_12
Patentnummer
US04362728

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