Phosphorus oxychloride → 4-Chloro-8-nitrobenzo[4,5]thieno[3,2-b]pyridine-3-carbonitrile

HRID 2213764Notes

Reaction equation

HRID 2213764 reaction equation
O[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[C:10]3[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:11]=3[S:12][C:3]=12.P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[C:10]3[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:11]=3[S:12][C:3]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178510326HCID 178510326, compound

Product 1

HCID 109571994-Chloro-8-nitrobenzo[4,5]thieno[3,2-b]pyridine-3-carbonitrileYield 73%

Procedure

A mixture of 1.22 g (4.49 mmol) of 4-hydroxy-8-nitrobenzo[4,5]thieno[3,2-b]pyridine-3-carbonitrile in 20 mL of phosphorous oxychloride is heated at reflux temperature for 3 hours, then cooled to room temperature. The solid is collected by filtration, then washed with hexane followed by water. The solid is dried to give 947 mg (73%) of a dark brown solid, mp softens at 270° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 3 hours
  3. filtrationThe solid is collected by filtration
  4. washwashed with hexane
  5. customThe solid is dried

Sources & evidence

ORD record
ord-d4639dbfe32c45eeb4205a4411888ad0
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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