Hydrochloric Acid → HCID 178433297, compound

HRID 1862845Notes

Reaction equation

HRID 1862845 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][NH2:4].Cl.[OH-].[K+].[N+:10]([CH:13]=[C:14](S(C)=O)SC)([O-:12])=[O:11].[CH3:20][C:21]1[N:22]=[CH:23][NH:24][C:25]=1[CH2:26][S:27][CH2:28][CH2:29][NH2:30]>CO.O>[N+:10]([CH:13]=[C:14]([NH:30][CH2:29][CH2:28][S:27][CH2:26][C:25]1[NH:24][CH:23]=[N:22][C:21]=1[CH3:20])[NH:4][CH2:3][C:2]([F:6])([F:5])[F:1])([O-:12])=[O:11]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 14797Potassium HydroxideHCID 544870941-Nitro2-methylthio-2-methylsulphinylethyleneHCID 178433288HCID 178433288, compound

Product 1

HCID 178433297HCID 178433297, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent4×HCID 962WaterSolvent

Procedure

A solution of 2,2,2-trifluoroethylamine (4.0 g) from the hydrochloride and potassium hydroxide in methanol (45 ml) and water (5 ml) was added slowly to a suspension of 1-nitro-2-methylsulphinyl-2-methylthio ethylene (3.6 g) in methanol (150 ml) at 0°. The mixture was stirred at room temperature for 24 hours, concentrated and dissolved in chloroform. Filtration, redissolution in a small volume of chloroform and precipitation with hexane afforded an orange crystalline solid. This was dissolved in methanol (25 ml) and a solution of 4-methyl-5-[(2-aminoethyl)thiomethyl]imidazole (2.1 g) in methanol (25 ml) was added. The resulting solution was heated under reflux for 2 hours and set aside at room temperature for 18 hours. Concentration followed by chromatographic purification on a column of silica gel with chloroform-methanol (15.1) as eluant and final crystallisation from ethanol afforded the title compound as a hemi-ethanolate (2.4 g) m.p. 161° (dec).

Workup

  1. concentrationconcentrated
  2. dissolutiondissolved in chloroform
  3. filtrationFiltration, redissolution
  4. customin a small volume of chloroform and precipitation with hexane
  5. customafforded an orange crystalline solid
  6. temperatureThe resulting solution was heated
  7. temperatureunder reflux for 2 hours
  8. waitset aside at room temperature for 18 hours
  9. concentrationConcentration
  10. customfollowed by chromatographic purification on a column of silica gel with chloroform-methanol (15.1) as eluant
  11. customfinal crystallisation from ethanol

Sources & evidence

ORD record
ord-0da2ab740e5549c1ad264d73f320809f
Source dataset
uspto-grants-1979_09
Patent number
US04166856

Reaction notes

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