Sodium Hydroxide → 7-Chlorothieno[3,2-b]pyridine

HRID 525793Notes

Reaction equation

HRID 525793 reaction equation
[S:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2O)[CH:3]=[CH:2]1.P(Cl)(Cl)([Cl:13])=O.[OH-].[Na+]>>[Cl:13][C:8]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:3]=[CH:2][S:1][C:9]=12

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 5074765Thieno[3,2-b]pyridin-7-ol

Product 1

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

Procedure

Thieno[3,2-b]pyridin-7-ol (20 g, 0.132 mol) was suspended in phosphorous oxy chloride (80.9 g, 0.528 mol) and stirred at 100 C for 2 hours. The solution was cooled to room temperature and was poured over ice. The aqueous solution was neutralized with sodium hydroxide and the resulting precipitate was collected by filtration and washed with water. The filter cake was taken up in dichloromethane and dried over magnesium sulfate. The solution was filtered and the filtrate was concentrated to dryness to give 7-chlorothieno[3,2-b]pyridine as a brown liquid which solidified to a beige solid under high vacuum. Yield: 20.4 g (91%); MS [M+H]+ 169.9; 1HNMR (CDCl3) δ: 8.7 (d, 1H), 7.8 (d, 1H), 7.6 (d, 1H), 7.3 (d, 1H) ppm.

Workup

  1. additionwas poured over ice
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe solution was filtered
  6. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-5b0be704b05148e1a43bfe6e5d2e9cb0
Source dataset
uspto-grants-2016_05
Patent number
US09340555B2

Reaction notes

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