Methanol → HCID 178481705, compound

HRID 1088655Notes

Reaction equation

HRID 1088655 reaction equation
[C:1]([NH:5][NH2:6])(=O)[CH2:2][OH:3].[CH3:7][N:8]=[C:9]=[S:10].CO.[Na]>C(O)C>[OH:3][CH2:2][C:1]1[N:8]([CH3:7])[C:9]([SH:10])=[N:6][N:5]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 11167Methyl isothiocyanateHCID 3505362-HydroxyacetohydrazideHCID 5360545Sodium

Product 1

HCID 178481705HCID 178481705, compoundYield 35.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 9 g of glycolic acid hydrazide, 7.3 g of methyl isothiocyanate 50 ml of methanol and 50 ml of ethanol was heated under reflux for 5 hours. Following the addition of 2.3 g of sodium metal, the mixture was further refluxed for 24 hours. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in 150 ml of water and adjusted to pH 2.5 with phosphoric acid. The resultant crystals were collected by filtration and recrystallized from ethanol. By the above procedure there were obtained 5.2 g of the captioned compound. m.p. 199°-201° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. temperaturethe mixture was further refluxed for 24 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. dissolutionthe residue was dissolved in 150 ml of water
  6. filtrationThe resultant crystals were collected by filtration
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-b1cadaf218404344a18bca02bc805f1d
Source dataset
uspto-grants-1990_10
Patent number
US04963542

Reaction notes

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