Hydrochloric Acid → 1-tert-Butyl-1H-pyrazole

HRID 473319Notes

Reaction equation

HRID 473319 reaction equation
Cl.[CH3:2][C:3]([NH:6][NH2:7])([CH3:5])[CH3:4].CO[CH:10](OC)[CH2:11][CH:12](OC)OC.Cl>C(O)C.CO>[CH3:2][C:3]([N:6]1[CH:12]=[CH:11][CH:10]=[N:7]1)([CH3:5])[CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 66019TetramethoxypropaneHCID 81889tert-Butylhydrazine monohydrochloride

Product 1

HCID 134698151-tert-Butyl-1H-pyrazoleYield 20.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A mixture of (1,1-dimethylethyl)hydrazine hydrochloride (1.02 g, 8.19 mmol) (Aldrich), 1,1,3,3-tetrakis(methyloxy)propane (1.344 g, 8.19 mmol) (Aldrich) and hydrochloric acid (0.672 ml, 8.19 mmol) in ethanol (10 ml) was heated under reflux. A solution formed. After 16 h the reaction had gone to completion and so was concentrated in vacuo to yield the crude product. This was dissolved in methanol and passed through an aminopropyl cartridge (20 g), eluting with methanol. The combined filtrates were concentrated in vacuo to yield the title compound as a cream gum (210 mg)

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customA solution formed
  4. concentrationso was concentrated in vacuo
  5. customto yield the crude product
  6. washeluting with methanol
  7. concentrationThe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-c488f12d6c4a4cf9812dea55bb5b3fd5
Source dataset
uspto-grants-2014_01
Patent number
US08633319B2

Reaction notes

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