Cyanuric chloride → 4-Chlorothieno[2,3-b]pyridine-5-carbonitrile

HRID 1178613Notes

Reaction equation

HRID 1178613 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([NH2:10])=O)=[CH:6][N:5]=[C:4]2[S:11][CH:12]=[CH:13][C:3]=12.N1C(Cl)=NC(Cl)=NC=1Cl>CN(C)C=O>[Cl:1][C:2]1[C:7]([C:8]#[N:10])=[CH:6][N:5]=[C:4]2[S:11][CH:12]=[CH:13][C:3]=12

Participants

4

Reactant 2

HCID 7954Cyanuric chlorideHCID 111485614-Chlorothieno[2,3-B]pyridine-5-carboxamide

Product 1

HCID 114129074-Chlorothieno[2,3-b]pyridine-5-carbonitrileYield 63.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-chlorothieno[2,3-b]pyridine-5-carboxamide (145 mg, 0.68 mmol) and cyanuric chloride (200 mg, 1.08 mmol) in 5 mL of N,N-dimethylformamide is stirred at room temperature for 30 minutes. Ice is added to the reaction mixture and the resultant solids are collected by filtration washing with water to provide 84 mg of 4-chlorothieno[2,3-b]pyridine-5-carbonitrile as a white solid, mp 100–103° C.; 1H NMR (DMSO-d6) δ 7.66 (d, J=6 Hz, 1H), 8.26 (d, J=6 Hz, 1H), 9.03 (s, 1H); MS 195.0 (M+H)+.

Workup

  1. additionIce is added to the reaction mixture
  2. filtrationthe resultant solids are collected by filtration
  3. washwashing with water

Sources & evidence

ORD record
ord-68cbe3a5969d4df98e87fabf9a0fb916
Source dataset
uspto-grants-2007_10
Patent number
US07276519B2

Reaction notes

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