Phenylhydrazine → 5-(2-methyl-propenyl)-1-phenyl-3-pyrrolidin-1-yl-1H-[1,2,4]triazole

HRID 1055017Notes

Reaction equation

HRID 1055017 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.[C:16]1([NH:22][NH2:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(OCC)(=O)C>[CH3:13][C:12]([CH3:14])=[CH:11][C:10]1[N:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:23]=[C:3]([N:4]2[CH2:8][CH2:7][CH2:6][CH2:5]2)[N:9]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 178503950HCID 178503950, compound

Product 1

HCID 900265325-(2-methyl-propenyl)-1-phenyl-3-pyrrolidin-1-yl-1H-[1,2,4]triazoleYield 38.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-methyl-but-2-enoic acid 1-methylsulfanyl-1-pyrrolidin-1-yl-meth-(Z)-ylideneamide (130 mg, 0.575 mmol) and phenyl hydrazine (0.6 ml, 5.75 mmol) was stirred for 3 hours at 100° C. The mixture was cooled, diluted with ethyl acetate and washed twice with water. The organic layer was separated, dried over sodium sulfate, filtered and concentrated. The crude material was purified by silica gel column chromatography using 50% ethyl acetate in hexane affording 5-(2-methyl-propenyl)-1-phenyl-3-pyrrolidin-1-yl-1H-[1,2,4]triazole (60 mg, 38.87%) as colorless liquid. MS: m/z=268.8 (M+H+)

Workup

  1. temperatureThe mixture was cooled
  2. washwashed twice with water
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-37503e7efce5415699813d66145e4013
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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