Methyl iodide → 5-Methyl-4,5-dihydrotetrazolo[1,5-a]quinoxaline

HRID 1576014Notes

Reaction equation

HRID 1576014 reaction equation
[N:1]1[N:5]2[C:6]3[C:11]([NH:12][CH2:13][C:4]2=[N:3][N:2]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3.[CH3:14]I.[H-].[Na+]>C(COC)OC>[CH3:14][N:12]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]2[N:1]=[N:2][N:3]=[C:4]2[CH2:13]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 215140494,5-Dihydrotetrazolo[1,5-a]quinoxaline

Product 1

HCID 215140505-Methyl-4,5-dihydrotetrazolo[1,5-a]quinoxaline

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 1 g. of 4,5-dihydrotetrazolo[1,5-a]quinoxaline and 2 g. of methyl iodide in 50 ml. of dimethoxyethane was stirred with 1.5 g. of sodium hydride, as a 50 percent suspension in mineral oil, overnight at room temperature. The reaction mixture was then filtered and evaporated under vacuum. The residue was dissolved in ethyl acetate and extracted twice with water. The brown residue which resulted on evaporation of the dried organic layer was washed with cyclohexane, leaving 0.87 g. of crude product. Two recrystallizations from ethanol produced pure 4,5-dihydro-5-methyltetrazolo[1,5-a]quinoxaline, m.p. 107°-10°C., which was identified by NMR analysis and elemental micro-analysis with the following results.

Workup

  1. customin mineral oil, overnight
  2. customat room temperature
  3. filtrationThe reaction mixture was then filtered
  4. customevaporated under vacuum
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. extractionextracted twice with water
  7. customThe brown residue which resulted on evaporation of the dried organic layer
  8. washwas washed with cyclohexane
  9. customleaving 0.87 g
  10. customTwo recrystallizations from ethanol produced pure 4,5-dihydro-5-methyltetrazolo[1,5-a]quinoxaline, m.p. 107°-10°C., which

Sources & evidence

ORD record
ord-f2b7f37b6fa34332a823c68342da3da8
Source dataset
uspto-grants-1976_09
Patent number
US03979387

Reaction notes

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