Formaldehyde → HCID 13469410, compound

HRID 2290269Notes

Reaction equation

HRID 2290269 reaction equation
[C:1]([BH3-])#[N:2].[Na+].N[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]([CH3:19])[NH:14][C:15](=[O:18])[NH:16][N:17]=2)=[CH:8][CH:7]=1.[CH2:20]=O>C(O)(=O)C.CO>[CH3:20][N:2]([CH3:1])[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]([CH3:19])[NH:14][C:15](=[O:18])[NH:16][N:17]=2)=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 133860336-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one

Product 1

HCID 13469410HCID 13469410, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride (0.62 g) was added portionwise to a solution of 6-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (1 g) and 36% aqueous formaldehyde (0.92 ml) in a mixture of acetic acid (20 ml) and methanol (30 ml) at room temperature. After stirring for 0.5 hours at the same temperature, the reaction mixture was evaporated in vacuo. To the oily residue was added an aqueous solution of sodium bicarbonate, and the resultant solid was collected by filtration and recrystallized from 70% aqueous ethanol to give 6-(4-dimethylaminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (0.8 g).

Workup

  1. customthe reaction mixture was evaporated in vacuo
  2. additionTo the oily residue was added an aqueous solution of sodium bicarbonate
  3. filtrationthe resultant solid was collected by filtration
  4. customrecrystallized from 70% aqueous ethanol

Sources & evidence

ORD record
ord-27b4b0640f004bb2b5c2faf4863e07e4
Source dataset
uspto-grants-1986_10
Patent number
US04616015

Reaction notes

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