Hexane → HCID 10824241, compound

HRID 2213756Notes

Reaction equation

HRID 2213756 reaction equation
O[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[S:12][C:3]=12.CCCCCC.P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[S:12][C:3]=12

Participants

4

Reactant 3

HCID 8058HexaneHCID 24813Phosphorus oxychlorideHCID 178510325HCID 178510325, compound

Product 1

HCID 10824241HCID 10824241, compoundYield 64%

Procedure

A mixture of 1.01 g (4.47 mmol) of 4-hydroxybenzo[4,5]thieno[3,2-b]pyridine-3-carbonitrile in 7 mL of phosphorous oxychloride is heated at reflux temperature for 40 minutes, then cooled to room temperature. Hexane is added and the solid is collected by filtration, dissolved in ethyl acetate and washed with saturated sodium bicarbonate. The organic layer is dried over magnesium sulfate, filtered and concentrated in vacuo to a small volume. The solids are collected by filtration to give 696 mg (64%) of product, mp 305–308° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 40 minutes
  3. filtrationthe solid is collected by filtration
  4. dissolutiondissolved in ethyl acetate
  5. washwashed with saturated sodium bicarbonate
  6. dry with materialThe organic layer is dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to a small volume
  9. filtrationThe solids are collected by filtration

Sources & evidence

ORD record
ord-f6be563b00154344930b580950f76f44
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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