tert-Butylhydrazine monohydrochloride → HCID 19775373, compound

HRID 1613158Notes

Reaction equation

HRID 1613158 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH2:12][CH2:13][CH3:14])[C:4](=[O:15])[C:3]=1[C:16]#[N:17].Cl.[C:19]([NH:23][NH2:24])([CH3:22])([CH3:21])[CH3:20]>C(O)C.C(N(CC)CC)C>[NH2:17][C:16]1[N:23]([C:19]([CH3:22])([CH3:21])[CH3:20])[N:24]=[C:2]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N:5]([CH2:12][CH2:13][CH3:14])[C:4](=[O:15])[C:3]=12

Participants

5

Reactant 2

HCID 81889tert-Butylhydrazine monohydrochlorideHCID 19775370HCID 19775370, compound

Product 1

HCID 19775373HCID 19775373, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

In a mixture of 60 ml of ethanol and 5 ml of triethylamine, 2.00 g (8.1 mmol) of Compound b and 2.00 g (16 mmol) of t-butylhydrazine hydrochloride were refluxed for 4 hours. The reaction mixture was dried under reduced pressure, and the residue was partitioned between chloroform and water. The chloroform layer was dried under reduced pressure, and the residue was passed through a silica gel column and eluted with a 3:1 (by volume) mixed solvent of hexane and ethyl acetate. The main fraction collected was dried under reduced pressure to obtain 2.11 g (87%) of Compound 7 as a colorless crystal. The product was treated with ethyl acetate saturated with hydrogen chloride to obtain a hydrochloride of Compound 7.

Workup

  1. temperaturewere refluxed for 4 hours
  2. customThe reaction mixture was dried under reduced pressure
  3. customthe residue was partitioned between chloroform and water
  4. dry with materialThe chloroform layer was dried under reduced pressure
  5. washeluted with a 3:1 (by volume)
  6. additionmixed solvent of hexane and ethyl acetate
  7. customThe main fraction collected
  8. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-8aacd31d39ec4748a257ffa62df2bdb1
Source dataset
uspto-grants-1993_03
Patent number
US05192768

Reaction notes

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