Sulfuric Acid → HCID 13883806, compound

HRID 543753Notes

Reaction equation

HRID 543753 reaction equation
[F:1][C:2]([F:21])([F:20])[CH2:3][N:4]=[C:5]([NH2:19])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH2:14][CH2:15][CH2:16][C:17]#[N:18])[N:8]=1.[OH:22]S(O)(=O)=O.[OH-].[Na+]>O>[F:21][C:2]([F:1])([F:20])[CH2:3][N:4]=[C:5]([NH2:19])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH2:14][CH2:15][CH2:16][C:17]([NH2:18])=[O:22])[N:8]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 21279772HCID 21279772, compound

Product 1

HCID 13883806HCID 13883806, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-[4-(2-[2,2,2-trifluoroethyl]guanidino)pyrimid-2-ylthio]butyronitrile (0.14 g.) and concentrated H2SO4 was left at room temperature for 3 hours and then diluted with crushed ice and water. The solution was basified with 10 N aqueous NaOH and the mixture extracted three times with EtOAc. The combined extracts were dried and evaporated to dryness to give 4-[4-(2-[2,2,2-trifluoroethyl]guanidino)pyrimid-2-ylthio]butyramide (0.13 g.) which was characterised as the hydrogen maleate, m.p. 202°-203° on recrystallisation from aqueous EtOH.

Workup

  1. extractionthe mixture extracted three times with EtOAc
  2. customThe combined extracts were dried
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-7db3eaa63e3d45c0b5c6d1e580d653b7
Source dataset
uspto-grants-1984_05
Patent number
US04447441

Reaction notes

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