Phosphorus oxychloride → HCID 14207943, compound

HRID 580531Notes

Reaction equation

HRID 580531 reaction equation
[N+:1]([C:4]1[C:5](=O)[C:6]2[CH:12]=[CH:11][S:10][C:7]=2[NH:8][CH:9]=1)([O-:3])=[O:2].P(Cl)(Cl)([Cl:16])=O>>[Cl:16][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=[C:7]2[S:10][CH:11]=[CH:12][C:6]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 14207939HCID 14207939, compound

Product 1

HCID 14207943HCID 14207943, compoundYield 94%

Conditions

Temperature
115 °C

Procedure

A mixture of 3.4 g of 5-nitrothieno[2,3-b]pyridin-4(7H)-one 6 and 34 ml of phosphorus oxychloride is heated at 115° C. (bath temperature) for 1 hour and evaporated to dryness in vacuo. The residue is taken up in chloroform and washed with water. The organic phase is dried over magnesium sulfate and concentrated in vacuo. The residue is purified by column chromatography on silica gel. Elution with dichloromethane-ether (50:1 v/v) affords 3.51 g (94%) of Compound 7 as crystals melting at 110°-113° C.

Workup

  1. customevaporated to dryness in vacuo
  2. washwashed with water
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by column chromatography on silica gel
  6. washElution with dichloromethane-ether (50:1 v/v)

Sources & evidence

ORD record
ord-edb684c8527b4b16b7150f513a9c56c5
Source dataset
uspto-grants-1988_06
Patent number
US04753951

Reaction notes

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