Pyrazole → 1-(2-oxiranylmethyl)-1H-pyrazole

HRID 2263447Notes

Reaction equation

[OH-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[N:4]1.[CH2:8]([CH:10]1[O:12][CH2:11]1)Cl>>[O:12]1[CH2:11][CH:10]1[CH2:8][N:3]1[CH:7]=[CH:6][CH:5]=[N:4]1

Participants

Reactant 3

HCID 1048Pyrazole

HCID 7835Epichlorohydrin

HCID 14798Sodium Hydroxide

Product 1

HCID 126036811-(2-oxiranylmethyl)-1H-pyrazole

Procedure

Compounds of formula 2. Reaction of sodium hydroxide with appropriate 1H-pyrazole starting material in neat epichlorohydrin at room temperature furnishes the corresponding 1-oxiranylmethyl-1H-pyrazole compound. To this product is added distilled water and an excess of secondary amine. The reaction mixture is then heated at moderate to high temperature (˜80° C.) for several hours. After suitable work-up (typically column chromatography), the corresponding 1-amino-3-(pyrazol-1-yl)-propan-2-ol compound is isolated.

Sources & evidence

ORD record: ord-9d65393e4d194acaba62fe22a467e4a3
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851570B2

Reaction notes

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