Hydrazine → 5-(2-Methyl-propenyl)-3-pyrrolidin-1-yl-1H-[1,2,4]triazole

HRID 1055019Notes

Reaction equation

HRID 1055019 reaction equation
CS/[C:3](=[N:9]\[C:10](=O)[CH:11]=[C:12]([CH3:14])[CH3:13])/[N:4]1[CH2:8][CH2:7][CH2:6][CH2:5]1.[NH2:16][NH2:17]>>[CH3:13][C:12]([CH3:14])=[CH:11][C:10]1[NH:17][N:16]=[C:3]([N:4]2[CH2:8][CH2:7][CH2:6][CH2:5]2)[N:9]=1

Participants

3

Reactant 2

HCID 9321HydrazineHCID 178503950HCID 178503950, compound

Product 1

HCID 900176975-(2-Methyl-propenyl)-3-pyrrolidin-1-yl-1H-[1,2,4]triazoleYield 29.39%

Conditions

Temperature
100 °C

Procedure

A mixture of 3-methyl-but-2-enoic acid 1-methylsulfanyl-1-pyrrolidin-1-yl-meth-(Z)-ylidene amide (1.2 g, 5.3 mmol) and hydrazine solution was stirred for 2 hours at 100° C. in a sealed tube. The mixture was cooled and concentrated. The crude material was purified by combiflash column chromatography using 50% ethyl acetate in hexane to give 5-(2-methyl-propenyl)-3-pyrrolidin-1-yl-1H-[1,2,4]triazole (300 mg, 29.39%) as a white solid. MS: m/z=193 (M+H+)

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. customThe crude material was purified by combiflash column chromatography

Sources & evidence

ORD record
ord-16931a0f0a6341329ad0442cfa5b8745
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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