Cyanuric chloride → 7-Chlorothieno[3,2-b]pyridine-6-carbonitrile

HRID 1611477Notes

Reaction equation

HRID 1611477 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([NH2:10])=O)=[CH:6][N:5]=[C:4]2[CH:11]=[CH:12][S: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[CH:11]=[CH:12][S:13][C:3]=12

Participants

4

Reactant 2

HCID 7954Cyanuric chlorideHCID 114016017-Chlorothieno[3,2-B]pyridine-6-carboxamide

Product 1

HCID 118164017-Chlorothieno[3,2-b]pyridine-6-carbonitrileYield 90.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-chlorothieno[3,2-b]pyridine-6-carboxamide (10.8 g, 51 mmol) in 80.0 mL of N,N-dimethylformamide is added cyanuric chloride (5.72 g, 31 mmol). After 30 minutes the suspension is poured into ice water. The solid is filtered, washed with ice water and dried in vacuo to give 9.0 g of 7-chlorothieno[3,2-b]pyridine-6-carbonitrile as an off white solid, mp 105-107° C.; 1H NMR (DMSO-d6) δ 7.83 (s, 1H), 8.61 (s, 1H), 9.12 (s, 1H); MS 195.0, 197.0 (M+H)+.

Workup

  1. filtrationThe solid is filtered
  2. washwashed with ice water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-d6c303f3eb5449689ce392ad919c9c43
Source dataset
uspto-grants-2006_01
Patent number
US06987116B2

Reaction notes

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