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

HRID 2178740Notes

Reaction equation

HRID 2178740 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-0abf20417624463aaf815d0834d3bbe8
Source dataset
uspto-grants-2015_06
Patent number
US09067947B2

Reaction notes

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