1,1-Dimethylhydrazine → HCID 299783, compound

HRID 1729604Notes

Reaction equation

HRID 1729604 reaction equation
[N:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:2].[CH3:9][N:10]([NH2:12])[CH3:11]>C(O)C>[CH3:9][N:10]([CH3:11])[N:12]=[N+:1]([O-:2])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 59761,1-DimethylhydrazineHCID 11473Nitrosobenzene

Product 1

HCID 299783HCID 299783, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of 7.5 g. of nitrosobenzene in 80 ml. of ethanol at 0° was added in a dropwise manner 4.2 g. of unsymmetrical-dimethylhydrazine as a saturated solution in ethanol. After stirring at 0° for 2 hours, the reaction mixture was allowed to warm to 25° C. and stirred for 16 hours longer. The solution was concentrated in vacuo, and the red-brown oil was chromatographed on silica gel in benzene. The product was eluted with 5-10 percent ethyl acetate in benzene. Three grams of 3,3-dimethyl-1-phenyltriazene-1-oxide was obtained as a light brown oil which gave a suitable n.m.r. spectrum.

Workup

  1. stirringstirred for 16 hours longer
  2. concentrationThe solution was concentrated in vacuo
  3. customthe red-brown oil was chromatographed on silica gel in benzene
  4. washThe product was eluted with 5-10 percent ethyl acetate in benzene

Sources & evidence

ORD record
ord-67888d494fa040e192812873e2f4a505
Source dataset
uspto-grants-1976_11
Patent number
US03989680

Reaction notes

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