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

HRID 1178603Notes

Reaction equation

HRID 1178603 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-9bf9dad1e6154149979b41dd8c4669b8
Source dataset
uspto-grants-2007_10
Patent number
US07276519B2

Reaction notes

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