3,4(2H,5H)-Furandione, 2,2,5,5-tetramethyl- → 5,7-Dihydro-5,5,7,7-tetramethyl-3-(3-nitrophenyl)furo(3,4-e)-1,2,4-triazine

HRID 1657724Notes

Reaction equation

HRID 1657724 reaction equation
[CH3:1][C:2]1([CH3:11])[C:6](=O)[C:5](=O)[C:4]([CH3:10])([CH3:9])[O:3]1.[N+:12]([C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=1)[C:18]([NH:20][NH2:21])=[NH:19])([O-:14])=[O:13]>C(O)C>[CH3:1][C:2]1([CH3:11])[C:6]2[N:19]=[C:18]([C:17]3[CH:22]=[CH:23][CH:24]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=3)[N:20]=[N:21][C:5]=2[C:4]([CH3:10])([CH3:9])[O:3]1

Participants

4

Reactant 2

HCID 5507123,4(2H,5H)-Furandione, 2,2,5,5-tetramethyl-HCID 178512512HCID 178512512, compound

Product 1

HCID 1009575,7-Dihydro-5,5,7,7-tetramethyl-3-(3-nitrophenyl)furo(3,4-e)-1,2,4-triazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.56 g. (0.01 mole) of 2,2,5,5-tetramethyl-3,4(2H,5H) furandione and 1.80 g. (0.01 mole) 3-nitro benzimidic acid hydrazide in 100 ml. absolute ethanol is refluxed under nitrogen for 18 hours at a bath temperature of 100°C. The excess water is removed from the condensate by using a Dean Stark trap filled with 3A molecular sieves. The resulting mixture is evaporated to dryness in vacuo at 40°C., and the resulting residue is recrystallized from hexane to give 5,7-dihydro-5,5,7,7-tetramethyl-3-(m-nitrophenyl)furo[3,4-e]-as-triazine.

Workup

  1. additionA mixture of 1.56 g
  2. customThe excess water is removed from the condensate
  3. additionfilled with 3A molecular sieves
  4. customThe resulting mixture is evaporated to dryness in vacuo at 40°C.
  5. customthe resulting residue is recrystallized from hexane

Sources & evidence

ORD record
ord-e880f2f5b4e04d2682b536c17149c000
Source dataset
uspto-grants-1976_06
Patent number
US03962240

Reaction notes

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