3,3-Difluoroazetidine-1-carbonitrile → 1-(1H-Benzotriazol-1-yl)-1-(3,3-difluoroazetidin-1-yl)methanimine

HRID 75562Notes

Reaction equation

HRID 75562 reaction equation
[F:1][C:2]1([F:8])[CH2:5][N:4]([C:6]#[N:7])[CH2:3]1.[NH:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[N:10]1>ClCCCl>[N:9]1([C:6]([N:4]2[CH2:5][C:2]([F:8])([F:1])[CH2:3]2)=[NH:7])[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[N:10]1

Participants

4

Reactant 2

HCID 866847033,3-Difluoroazetidine-1-carbonitrileHCID 178418385HCID 178418385, compound

Product 1

HCID 866847021-(1H-Benzotriazol-1-yl)-1-(3,3-difluoroazetidin-1-yl)methanimineYield 59.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3,3-difluoroazetidine-1-carbonitrile (135 mg, 1.14 mmol) and benzotriazole (136 mg, 1.14 mmol) in 1,2-dichloroethane (0.2 mL) was heated to 80° C. under nitrogen for 30 min. A needle was inserted to facilitate evaporation of the solvent and the mixture was heated at 80° C. for 45 min. The resulting solids were washed with ether (2×3 mL) and dried under reduced pressure to give the title compound as an off-white solid (160 mg, 51%).

Workup

  1. customevaporation of the solvent
  2. temperaturethe mixture was heated at 80° C. for 45 min
  3. washThe resulting solids were washed with ether (2×3 mL)
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-2811bb9960fa440ca70ba2e6b77f9bfa
Source dataset
uspto-grants-2014_09
Patent number
US08835449B2

Reaction notes

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