Phosphorus oxychloride → 7-Chlorothieno[3,2-b]pyridine-6-carbonitrile

HRID 1468993Notes

Reaction equation

HRID 1468993 reaction equation
O=[C:2]1[C:7]([C:8]#[N:9])=[CH:6][NH:5][C:4]2[CH:10]=[CH:11][S:12][C:3]1=2.P(Cl)(Cl)([Cl:15])=O.C([O-])(O)=O.[Na+]>ClCCl>[Cl:15][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[CH:10]=[CH:11][S:12][C:3]=12

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 123948007-Oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carbonitrile

Product 1

HCID 118164017-Chlorothieno[3,2-b]pyridine-6-carbonitrileYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred mixture of 7-oxo-4,7-dihydro-thieno[3,2-b]pyridine-6-carbonitrile (0.668 g, 3.8 mmol) and 6 ml of phosphorus oxychloride was heated to reflux for 2 h, and then cooled to room temperature. The residue was added to ice water and dichloromethane, and the resulting mixture was neutralized by addition of solid NaHCO3 carefully. The organic layer was separated, washed with H2O, dried over MgSO4, and concentrated in vacuum to give 0.526 g (71%) of a red-brown solid. 1H NMR (300 MHz, DMSO-d6) δ 9.12 (s, 1H), 8.60 (d, J=5.4 Hz, 1H), 7.82 (d, J=6 Hz, 1H); LC-MS (ESI) m/z 195.0 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. customThe organic layer was separated
  4. washwashed with H2O
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-d1b8576697c24566b9c800882ce3b797
Source dataset
uspto-grants-2015_04
Patent number
US09006252B2

Reaction notes

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