Dimethylformamide → 4,5-Dibromothiophene-2-carbonitrile
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH2:10])=O)[S:5][C:6]=1[Br:7].CN(C=O)C.N1C(Cl)=NC(Cl)=NC=1Cl>O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]#[N:10])[S:5][C:6]=1[Br:7]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
An oven-dried round-bottomed flask was charged with 4,5-dibromothiophene-2-carboxamide (4.28 g, 15.0 mmol) and 20 mL of DMF under an argon atmosphere. The solution was cooled on an ice-water bath, and cyanuric chloride (1.81 g, 9.8 mmol) was then added in one portion. After stirring at 0° C. for 1 h, the reaction mixture was warmed to room temperature, and stirred for a further 3 h. 100 mL of water was added. A white solid was formed, which was collected through suction filtration, washed with water, and dried together with phosphorous pentoxide under vacuum to afford 3.70 g (92%) of product.
Workup
- temperatureThe solution was cooled on an ice-water bath
- temperaturethe reaction mixture was warmed to room temperature
- stirringstirred for a further 3 h
- customA white solid was formed
- filtrationwhich was collected through suction filtration
- washwashed with water
- dry with materialdried together with phosphorous pentoxide under vacuum
Sources & evidence
- ORD record
- ord-f0b9f32756644b6796987a37866b72f5
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09012655B2
Reaction notes
Loading…