Phosphorus oxychloride → HCID 14207947, compound

HRID 580534Notes

Reaction equation

HRID 580534 reaction equation
[N+:1]([C:4]1[C:5](=O)[C:6]2[C:7](=[CH:10][S:11][CH:12]=2)[NH:8][CH:9]=1)([O-:3])=[O:2].P(Cl)(Cl)([Cl:16])=O>>[Cl:16][C:5]1[C:6]2[C:7](=[CH:10][S:11][CH:12]=2)[N:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 14207946HCID 14207946, compound

Product 1

HCID 14207947HCID 14207947, compoundYield 60%

Conditions

Temperature
105 °C

Procedure

A mixture of 3.00 g of 3-nitrothieno[3,4-b]pyridin-4(1H)-one 10 and 9 ml of phosphorous oxychloride is stirred at 105° C. (bath temperature) for 1 hour and evaporated to dryness in vacuo. The residue is taken up in chloroform and washed with aqueous ammonia and water. The organic phase is dried over magnesium sulfate and evaporated. The residue is purified by column chromatography on silica gel. Elution with dichloromethane-ether (50:1 v/v) affords 2.02 g (60%) of Compound 11. Recrystallization from ether-petroleum ether affords colorless crystals melting at 139°-140° C.

Workup

  1. customevaporated to dryness in vacuo
  2. washwashed with aqueous ammonia and water
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. customevaporated
  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-07bf349db82f4e0d8d5d8a1f174daa30
Source dataset
uspto-grants-1988_06
Patent number
US04753951

Reaction notes

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