Sulfuric Acid → 3-((Imino((2,2,2-trifluoroethyl)amino)methyl)amino)1H-pyrazole-1-pentamide

HRID 543756Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 543756
[F:1][C:2]([F:20])([F:19])[CH2:3][N:4]=[C:5]([NH2:18])[NH:6][C:7]1[CH:11]=[CH:10][N:9]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[N:17])[N:8]=1.S(=O)(=O)(O)[OH:22].[OH-].[Na+]>>[F:20][C:2]([F:1])([F:19])[CH2:3][N:4]=[C:5]([NH2:18])[NH:6][C:7]1[CH:11]=[CH:10][N:9]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([NH2:17])=[O:22])[N:8]=1

Komponenten

4

Edukt 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 13883780HCID 13883780, Verbindung

Produkt 1

HCID 1347783-((Imino((2,2,2-trifluoroethyl)amino)methyl)amino)1H-pyrazole-1-pentamide

Versuchsvorschrift

5-[3-(2-[2,2,2-Trifluoroethyl]guanidino)pyrazol-1-yl]valeronitrile (13 g.) was added over 10 minutes to concentrated sulphuric acid (65 ml.) with stirring. The resulting solution was kept at 20° for 18 hours then diluted with ice (300 ml.) and basified to pH 9 with 10.8 N sodium hydroxide. The mixture was extracted with EtOAc (3×200 ml.) and the extract was dried (MgSO4) and evaporated in vacuo to an oil which crystallised. The crude material was recrystallised from EtOAc to give 5-[3-(2-[2,2,2-trifluoroethyl]guanidino)pyrazol-1-yl]valeramide, m.p. 130°. The maleic acid salt was prepared in acetone, m.p. 183°-184°.

Aufarbeitung

  1. extractionThe mixture was extracted with EtOAc (3×200 ml.)
  2. dry with materialthe extract was dried (MgSO4)
  3. customevaporated in vacuo to an oil which
  4. customcrystallised
  5. customThe crude material was recrystallised from EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-622b75a1b50a46d19829a3132d7bc6e4
Quelldatensatz
uspto-grants-1984_05
Patentnummer
US04447441

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