HCID 86643578, compound → 1-Chloro[1]benzothieno[2,3-c]pyridine

HRID 1848958Notes

Reaction equation

HRID 1848958 reaction equation
[Cl:1][C:2]1[C:7]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:6](N)[CH:5]=[CH:4][N:3]=1>CC(O)=O>[Cl:1][C:2]1[C:7]2[S:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 1

HCID 86643578HCID 86643578, compound

Product 1

HCID 8198151-Chloro[1]benzothieno[2,3-c]pyridineYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a 250 mL round flask was added 2-chloro-3-phenylthio-4-aminopyridine (2.7 g, 11.4 mmol), and 60 mL of glacial AcOH. To this clear solution, ButONO (1.36 g, 11.45 mmol) was added drop by drop. After stirring at room temperature for 1 h, another (1.36 g 11.45) mmol of ButONO was added. The mixture was continued to stir at room temperature for 18 h. The reaction was quenched by water, and the product was purified by a silica gel column. Yield (88%) of 1-chloro-benzothieno[2,3-c]pyridine was 2.2 g.

Workup

  1. additionTo this clear solution, ButONO (1.36 g, 11.45 mmol) was added drop by drop
  2. stirringto stir at room temperature for 18 h
  3. customThe reaction was quenched by water
  4. customthe product was purified by a silica gel column

Sources & evidence

ORD record
ord-42ea29f4d52b4257b236da1d9ba6a672
Source dataset
uspto-grants-2015_02
Patent number
US08952363B2

Reaction notes

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