Ammonia → HCID 23046142, compound

HRID 2107630Notes

Reaction equation

HRID 2107630 reaction equation
[C:1]([C:6]1[C:7](=O)[C:8]2[S:14][CH:13]=[CH:12][C:9]=2[NH:10][CH:11]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].N.P(Cl)(Cl)([Cl:19])=O>>[C:1]([C:6]1[C:7]([Cl:19])=[C:8]2[S:14][CH:13]=[CH:12][C:9]2=[N:10][CH:11]=1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 23046146HCID 23046146, compound

Product 1

HCID 23046142HCID 23046142, compound

Procedure

6-Butyrylthieno[3,2-b]pyridin-7(4H)-one (7.9 g, 0.0357 mol) and phosphorus oxychloride (30 ml) were heated under reflux for 1 hour. After allowing to cool the reaction mixture was poured onto ice basified with concentrated ammonia solution and extracted with dichloromethane (3×150 ml). The combined dichloromethane extracts were dried, filtered and evaporated to dryness to give 6-butyryl-7-chlorothieno[3,2-b]pyridine, 5.5 g. Recrystallization from hexane gave an analytically pure sample, m.p. 78°-80°.

Workup

  1. temperatureunder reflux for 1 hour
  2. temperatureto cool the reaction mixture
  3. additionwas poured onto ice
  4. extractionextracted with dichloromethane (3×150 ml)
  5. dry with materialThe combined dichloromethane extracts were dried
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-ba0470ed86d343cb86a9e19da38b5aed
Source dataset
uspto-grants-1990_06
Patent number
US04935431

Reaction notes

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