Dimethylformamide → 7-Chlorothieno[3,2-b]pyridine

HRID 2175382Notes

Reaction equation

HRID 2175382 reaction equation
Cl[CH:2]([Cl:4])[CH3:3].CN(C)C=O.C(Cl)(=O)C(Cl)=O.[S:16]1C2C(=O)[CH:22]=[CH:21][NH:20][C:19]=2[CH:18]=[CH:17]1>ClCCl>[Cl:4][C:2]1[CH:22]=[CH:21][N:20]=[C:19]2[CH:18]=[CH:17][S:16][C:3]=12

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 63651,1-DichloroethaneHCID 65578Oxalyl chlorideHCID 5074765Thieno[3,2-b]pyridin-7-ol

Product 1

HCID 112752517-Chlorothieno[3,2-b]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

30 ml of dichloromethane and 20 ml of dichloroethane in 250 ml round bottom flask were added with dimethylformamide (1.8 ml, 23.28 mmol) and oxalylchloride (2.9 ml, 33.86 mmol) was slowly dropped to the mixture at 0° C. After 4H-thieno[3,2-b]pyridine-7-one (1.6 g, 10.58 mmol) was added, the mixture was refluxed for 6 hours. After lowering the temperature to room temperature, the title compound of yellowish solid (1.7 g, 90%) was obtained.

Workup

  1. additionwas slowly dropped to the mixture at 0° C
  2. temperaturethe mixture was refluxed for 6 hours
  3. customto room temperature

Sources & evidence

ORD record
ord-6eaa8e5b99f74b469daa9b162c9a319d
Source dataset
uspto-grants-2015_06
Patent number
US09062066B2

Reaction notes

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