Sodium borohydride → HCID 15586358, compound

HRID 2290350Notes

Reaction equation

HRID 2290350 reaction equation
[BH4-].[Na+].[OH:3][CH2:4][C:5]([NH:7][NH:8][C:9]1[N:10]=[N:11][C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:13]([CH3:15])[N:14]=1)=[O:6]>CO>[OH:3][CH2:4][C:5]([NH:7][NH:8][C:9]1[NH:10][N:11]=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:13]([CH3:15])[N:14]=1)=[O:6]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 53899066HCID 53899066, compound

Product 1

HCID 15586358HCID 15586358, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.494 ) was added portionwise to a stirred solution of 3-(2-hydroxyacetylhydrazino)-5-methyl-6-phenyl-1,2,4-triazine (1.684 g) in methanol (30 ml) under ice cooling in 10 minutes and the stirring was continued for 1.5 hours at the same temperature. The reaction mixture was evaporated and the residue was dissolved in water. The solution was passed through a column of DIAION HP-20 (Trademark, manufactured by Mitsubishi Chemical Industries Ltd.) (80 ml) and eluted with water and then with methanol. The methanol eluate was evaporated under reduced pressure and the residual solid was recrystallized from methanol to give colorless crystals of 3-(2-hydroxyacetylhydrazino)-5-methyl-6-phenyl-2,5-dihydro-1,2,4-triazine (0.644 g), m.p. 167°~168° C. (decomp.)

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionthe residue was dissolved in water
  3. wash(Trademark, manufactured by Mitsubishi Chemical Industries Ltd.) (80 ml) and eluted with water
  4. customThe methanol eluate was evaporated under reduced pressure
  5. customthe residual solid was recrystallized from methanol

Sources & evidence

ORD record
ord-111b964f0da4403b830e896a65aa6e8b
Source dataset
uspto-grants-1986_10
Patent number
US04616014

Reaction notes

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