Hydrochloric Acid → HCID 18955296, compound

HRID 2380294Notes

Reaction equation

HRID 2380294 reaction equation
C[N:2](C)[CH:3]=[C:4]([S:7][CH3:8])[C:5]#N.[NH:10]([CH2:12][CH2:13][OH:14])[NH2:11].Cl>C(O)C>[OH:14][CH2:13][CH2:12][N:10]1[C:3]([NH2:2])=[C:4]([S:7][CH3:8])[CH:5]=[N:11]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 80172-HydrazinoethanolHCID 12732595HCID 12732595, compound

Product 1

HCID 18955296HCID 18955296, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 3-dimethylamino-2-methylthioacrylonitrile (5 g) and 2-hydrazinoethanol (2.68 g) in ethanol (50 ml) was added conc. hydrochloric acid (2.93 ml) under ice-cooling. The mixture was refluxed for 3 hours. The reaction mixture was evaporated to remove the solvent. The residue was adjusted to pH 7 with a saturated aqueous solution of sodium bicarbonate and extracted with a mixture of tetrahydrofuran and ethyl acetate. The organic layer was dried over magnesium sulfate. The solvent was removed in vacuo and the residue was subjected to column chromatography on silica gel using ethyl acetate as an eluent. Fractions containing the object compound were combined and evaporated to give 1-(2-hydroxyethyl)-4-methylthio-5-aminopyrazole (2.4 g).

Workup

  1. temperaturecooling
  2. temperatureThe mixture was refluxed for 3 hours
  3. customThe reaction mixture was evaporated
  4. customto remove the solvent
  5. extractionextracted with a mixture of tetrahydrofuran and ethyl acetate
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. customThe solvent was removed in vacuo
  8. additionFractions containing the object compound
  9. customevaporated

Sources & evidence

ORD record
ord-4ed4fafebe804ebfad1c5d5ee627cac6
Source dataset
uspto-grants-1994_11
Patent number
US05366970

Reaction notes

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