Water → 7-Chlorothieno[3,2-b]pyridine

HRID 1192295Notes

Reaction equation

HRID 1192295 reaction equation
CN(C=O)C.[C:6]([Cl:11])(=O)[C:7](Cl)=O.[N:12]1[C:17]2[CH:18]=[CH:19][S:20][C:16]=2C(=O)N[CH:13]=1.O>C(Cl)Cl>[Cl:11][C:6]1[CH:7]=[CH:13][N:12]=[C:17]2[CH:18]=[CH:19][S:20][C:16]=12

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 1354174223H,4H-thieno[3,2-d]pyrimidin-4-one

Product 1

HCID 112752517-Chlorothieno[3,2-b]pyridineYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of DMF (13.2 mL, 170 mmol) in DCM (100 mL) at 0° C. was added oxalyl chloride (22 mL, 252 mmol) in DCM (100 mL) very slowly over 1 hour. To the resulting white gel solution was added the 3H-thieno[3,2-d]pyrimidin-4-one (12 g, 79 mmol). The mixture was refluxed for 4 hours. After cooling, the mixture was purred into water (500 mL) and extracted with DCM (3×250 mL). Then the organic phase was dried over magnesium sulfate, filtered and concentrated to afford 7-chloro-thieno[3,2-b]pyridine as white solid (13.4 g, 99%). 1H NMR (CDCl3, 400 Hz) δ 9.00 (s, 1H), 8.06 (d, J=5.6 Hz, 1H), 7.61 (d, J=5.6 Hz, 1H). MS (ESI+) [M+H]+ 170

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. temperatureAfter cooling
  3. extractionextracted with DCM (3×250 mL)
  4. dry with materialThen the organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7a153654fa4a4e249d756dd161b191cd
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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