1,1-Dimethylhydrazine → HCID 54468337, compound

HRID 478053Notes

Reaction equation

HRID 478053 reaction equation
[CH3:1][O:2][C:3](=[CH2:6])[CH:4]=O.[CH3:7][N:8]([CH3:10])[NH2:9]>CCOCC>[CH3:1][O:2][C:3]([CH:4]=[N:9][N:8]([CH3:10])[CH3:7])=[CH2:6]

Participants

4

Reactant 2

HCID 59761,1-DimethylhydrazineHCID 113893562-Propenal, 2-methoxy-

Product 1

HCID 54468337HCID 54468337, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

6.4 g of 2-methoxyacrolein are stirred for 1 hour at 30°-35° C. with 4.4 g of N,N-dimethylhydrazine in 50 ml of ether, dried at 20° C. with Na2SO4 and then the solvent is removed. Distillation at 74°-76° C./13 mbar gives 6.2 g of pure 2-methoxy-4-dimethylamino-4-azabutadiene. (b) 10.8 g of 2-methoxy-4-dimethylamino-4-azabutadiene and 15 g of 2-tert.-butylisothiazolin-3-one-1,1-dioxide are stirred for 11/2 h at 80°-85° C. in 250 ml of toluene. The crude bicyclic compound of formula IVb is further processed in the crude state as described in Example 4. ##STR16## The compounds listed in Table 1 are obtained in an analogous manner.

Workup

  1. dry with materialdried at 20° C. with Na2SO4
  2. customthe solvent is removed
  3. distillationDistillation at 74°-76° C./13 mbar

Sources & evidence

ORD record
ord-e749b4b34a7b450e86acbdbeed1004cb
Source dataset
uspto-grants-1989_12
Patent number
US04889933

Reaction notes

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