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

HRID 1930345Notes

Reaction equation

HRID 1930345 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 (37 g, 226 mmol), tert-butyl-hydrazine hydrochloride (28 g, 226 mmol) and cone HCl (60 mL, 720 mmol) in EtOH (300 mL) was heated at reflux overnight. The mixture was poured into water and the resulting mixture was extracted with ether. The combined organics were washed with brine, dried (MgSO4) and concentrated in vacuo to give 1-tert-butyl-1H-pyrazole (25 g, 89% yield). 1H NMR (400 MHz, DMSO-d6): δ7.73 (s, 1 H), 7.38 (s, 1 H), 6.17 (s, 1 H), 1.47 (s, 9 H); MS (ESI) m/z: 125.1[M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. extractionthe resulting mixture was extracted with ether
  4. washThe combined organics were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-88d29bcda39c486592dcf65b7ebbcedf
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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