Acetic Anhydride → 6-(4-formylaminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one

HRID 2290737Notes

Reaction equation

HRID 2290737 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]([CH3:22])[NH:17][C:18](=[O:21])[NH:19][N:20]=2)=[CH:11][CH:10]=1>C(O)=O>[CH:1]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]([CH3:22])[NH:17][C:18](=[O:21])[NH:19][N:20]=2)=[CH:13][CH:14]=1)=[O:3]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 133860336-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one

Product 1

HCID 133860516-(4-formylaminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Procedure

With ice-cooling and stirring, acetic anhydride (1.4 ml) was added dropwise to formic acid (0.7 ml) and the mixture was stirred at 50° C. for 15 minutes. This solution was added to a solution of 6-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (2.28 g) in formic acid (6 ml) with ice-cooling and stirring, followed by further stirring with ice-cooling for 50 minutes. The reaction mixture was poured into ice water and the resulting precipitate was collected by filtration and washed with water. The solid was recrystallized from dimethyl sulfoxide to give 6-(4-formylaminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (1.36 g).

Workup

  1. temperatureWith ice-cooling
  2. stirringthe mixture was stirred at 50° C. for 15 minutes
  3. temperaturecooling
  4. stirringstirring
  5. stirringby further stirring with ice-
  6. temperaturecooling for 50 minutes
  7. filtrationthe resulting precipitate was collected by filtration
  8. washwashed with water
  9. customThe solid was recrystallized from dimethyl sulfoxide

Sources & evidence

ORD record
ord-ac8e0c59d97b464aa9c210847f2a7044
Source dataset
uspto-grants-1986_10
Patent number
US04618610

Reaction notes

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