1,1-Dimethylhydrazine → N'-(5-chloroindan-1-ylidene)-N,N-dimethylhydrazine

HRID 1977820Notes

Reaction equation

HRID 1977820 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=O)[CH2:6][CH2:5]2.[CH3:12][N:13]([CH3:15])[NH2:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[N:14][N:13]([CH3:15])[CH3:12])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 59761,1-DimethylhydrazineHCID 6101p-Toluenesulfonic acidHCID 1425995-Chloro-1-indanone

Product 1

HCID 57200018N'-(5-chloroindan-1-ylidene)-N,N-dimethylhydrazine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

20 g of 5-chloroindan-1-one are dissolved in 600 ml of dry toluene and, after addition of 27.4 ml of N,N-dimethylhydrazine and 1 g of p-toluenesulfonic acid, boiled with a water trap for 4 h. The reaction mixture is concentrated in vacuo, and the residue is dissolved in ethyl acetate and washed with sodium bicarbonate solution and then with water. The organic phase is dried over sodium sulfate and concentrated in vacuo, and the residue is chromatographed on silica gel with ethyl acetate/heptane ½. N′-(5-chloroindan-1-ylidene)-N,N-dimethylhydrazine is obtained as an oil.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. washwashed with sodium bicarbonate solution
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customthe residue is chromatographed on silica gel with ethyl acetate/heptane ½

Sources & evidence

ORD record
ord-108fb2fe712e458dba64e7e62fd662e1
Source dataset
uspto-grants-2001_05
Patent number
US06235763B1

Reaction notes

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