Phosphorus oxychloride → HCID 14207940, compound

HRID 580528Notes

Reaction equation

HRID 580528 reaction equation
[N+:1]([C:4]1[C:5](=O)[C:6]2[CH:12]=[C:11]([CH3:13])[S:10][C:7]=2[NH:8][CH:9]=1)([O-:3])=[O:2].P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=[C:7]2[S:10][C:11]([CH3:13])=[CH:12][C:6]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 14207938HCID 14207938, compound

Product 1

HCID 14207940HCID 14207940, compoundYield 68%

Procedure

A mixture of 2.26 g of 5-nitro-2-methylthieno[2,3-b]pyridine-4(7H)-one 2 and 10 ml of phosphorus oxychloride is refluxed for 1 hour. The reaction mixture is concentrated to dryness in vacuo and the residue is taken up on ethyl acetate. The organic phase is dried over magnesium sulfate and treated with activated charcoal. The mixture is filtered and the solvent is evaporated in vacuo. The crude product is recrystallized from ethyl acetate-n-hexane to give 1.90 g (68%) of Compound 3 as colorless crystals melting at 96°-98° C.

Workup

  1. temperatureis refluxed for 1 hour
  2. concentrationThe reaction mixture is concentrated to dryness in vacuo
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. additiontreated with activated charcoal
  5. filtrationThe mixture is filtered
  6. customthe solvent is evaporated in vacuo
  7. customThe crude product is recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-242f5b5513854c3dac4181519ea8f3b2
Source dataset
uspto-grants-1988_06
Patent number
US04753951

Reaction notes

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