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

HRID 543756Notes

Reaction equation

HRID 543756 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Procedure

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°.

Workup

  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

Sources & evidence

ORD record
ord-622b75a1b50a46d19829a3132d7bc6e4
Source dataset
uspto-grants-1984_05
Patent number
US04447441

Reaction notes

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