tert-Butylhydrazine → 1-tert-Butyl-3-methyl-1H-pyrazol-5-amine

HRID 479261

Reaction equation

HRID 479261 reaction equation
[NH2:1]/[C:2](/[CH3:6])=[CH:3]\[C:4]#[N:5].[C:7]([NH:11]N)([CH3:10])([CH3:9])[CH3:8]>C(O)CCCC.C(OC(C)C)(C)C>[NH2:5][C:4]1[N:11]([C:7]([CH3:10])([CH3:9])[CH3:8])[N:1]=[C:2]([CH3:6])[CH:3]=1

Participants

5

Reactant 2

HCID 81890tert-ButylhydrazineHCID 5325263(2Z)-3-Amino-2-butenenitrile

Product 1

HCID 7372001-tert-Butyl-3-methyl-1H-pyrazol-5-amineYield 58.7%

Reagents, catalysts & solvents 2

HCID 62761-PentanolSolventHCID 7914Diisopropyl EtherSolvent

Procedure

To a solution of 16.4 g (0.2 mol) of 3-aminocrotononitrile in 100 cm3 of n-pentanol were added 19.4 g (0.22 mol) of tert-butylhydrazine. This solution was heated at reflux for 20 hours. The n-pentanol was subsequently distilled off under reduced pressure. A pale yellow solid was obtained, which was taken up in 100 cm3 of isopropyl ether at room temperature and filtered on a sinter funnel. After drying under vacuum at 40° C., 18 g of the expected product were obtained in the form of a pale yellow solid, the melting point of which was from 172 to 175° C.

Workup

  1. temperatureThis solution was heated
  2. temperatureat reflux for 20 hours
  3. distillationThe n-pentanol was subsequently distilled off under reduced pressure
  4. customA pale yellow solid was obtained
  5. filtrationfiltered on a sinter funnel
  6. customAfter drying under vacuum at 40° C.

Sources & evidence

ORD record
ord-5f659bbdaba1465e8c980b43da429edd
Source dataset
uspto-grants-2003_11
Patent number
US06645258B2

Linked notes

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