Water → HCID 23344798, compound

HRID 1579162Notes

Reaction equation

HRID 1579162 reaction equation
Cl.[C:2]([NH:6][NH2:7])([CH3:5])([CH3:4])[CH3:3].[C-:8]#[N:9].[Na+].O.[C:12]1(=O)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>C(O)C>[C:2]([NH:6][NH:7][C:12]1([C:8]#[N:9])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 7967CyclohexanoneHCID 8929Sodium CyanideHCID 81889tert-Butylhydrazine monohydrochloride

Product 1

HCID 23344798HCID 23344798, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a rapidly stirred solution of 24.8 grams (0.2 mole) of t-butylhydrazine hydrochloride and 9.8 grams (0.2 mole) of sodium cyanide in 100 ml. of deionized water in a 250 ml. 4-neck round bottom flask, was added a solution of 19.6 grams (0.2 mole) of cyclohexanone in 15 ml. of ethanol. The reaction was stirred for 5 hours at room temperature and then allowed to stand overnight. The next morning the reaction was stirred an additional hour and filtered. The product was dried at 30°C. in a vacuum oven and the yield was 36.3 grams (93.5%) of a white solid melting at 70°-73°C. The white solid evolves HCN on exposure to air over extended periods. The infrared spectrum contained strong NH bands, a cyano band, and did not contain any carbonyl or imino bands. The infrared spectrum was thus consistent with the structure of the desired hydrazo product.

Workup

  1. waitto stand overnight
  2. stirringThe next morning the reaction was stirred an additional hour
  3. filtrationfiltered
  4. customThe product was dried at 30°C. in a vacuum oven
  5. waitThe white solid evolves HCN on exposure to air over extended periods

Sources & evidence

ORD record
ord-a0ad2cbe8d1c4474ab4c0ae2bc7e22d7
Source dataset
uspto-grants-1976_01
Patent number
US03931143

Reaction notes

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