Ammonia → 7-Chlorothieno[3,2-b]pyridine-2-carboxamide

HRID 1042784Notes

Reaction equation

HRID 1042784 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([O-:13])=O)[S:10][C:3]=12.[Li+].C(Cl)Cl.C(Cl)(=O)C(Cl)=O.[NH3:24]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([NH2:24])=[O:13])[S:10][C:3]=12

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 23677819Lithium 7-chlorothieno[3,2-b]pyridine-2-carboxylate

Product 1

HCID 594272817-Chlorothieno[3,2-b]pyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 250 mL flask was charged with lithium 7-chlorothieno[3,2-b]pyridine-2-carboxylate (3.00 g, 13.7 mmol) and CH2Cl2 (100 ml) under nitrogen. DMF (cat) (0.100 ml) and oxalyl dichloride (1.49 ml, 17.1 mmol) were added dropwise, and the reaction mixture was stirred for 3 hours, and concentrated in vacuo. The brown solid was redissolved in CH2Cl2 (100 ml) and ammonia (gas) (0.233 g, 13.7 mmol) was gently bubbled through the reaction mixture for 5 minutes. The flask was then capped and stirred at room temperature overnight under closed atmosphere. The brown suspension was concentrated in vacuo and the resulting solid was taken up in water (to dissolve the starting material), then collected by filtration to give 7-chlorothieno[3,2-b]pyridine-2-carboxamide. MS m/z=213 [M+H]+. Calc'd for C8H5ClN25OS: 212.66.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe brown solid was redissolved in CH2Cl2 (100 ml)
  3. customThe flask was then capped
  4. stirringstirred at room temperature overnight
  5. customunder closed atmosphere
  6. concentrationThe brown suspension was concentrated in vacuo
  7. dissolutionto dissolve the starting material),
  8. filtrationthen collected by filtration

Sources & evidence

ORD record
ord-e6c9d75a9cdb4cec91d418012ff9151b
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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