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

HRID 57845

Reaction equation

HRID 57845 reaction equation
CO[CH:3](OC)[CH2:4][CH:5](OC)OC.Cl.[C:13]([NH:17][NH2:18])([CH3:16])([CH3:15])[CH3:14].Cl.O>CCO>[C:13]([N:17]1[CH:5]=[CH:4][CH:3]=[N:18]1)([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 66019TetramethoxypropaneHCID 81889tert-Butylhydrazine monohydrochloride

Product 1

HCID 134698151-tert-Butyl-1H-pyrazoleYield 89.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1,1,3,3-tetramethoxypropane (3.7 g, 22.6 mmol), tert-butylhydrazine hydrochloride (2.8 g, 22.6 mmol), and conc. HCl (6 mL, 72 mmol) in EtOH (30 mL) was heated at reflux overnight. The reaction mixture was poured into water and the resulting mixture was extracted with ether (30 mL×3). The combined organics was washed with brine (20 mL), dried over MgSO4, and concentrated under reduced pressure to afford 1-tert-butyl-1H-pyrazole as a white solid (2.5 g, 89%). MS (ESI) m/z: 125 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. extractionthe resulting mixture was extracted with ether (30 mL×3)
  4. washThe combined organics was washed with brine (20 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6a335cf3c39a4015825d004aca41beae
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Linked notes

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