O-Toluidine → HCID 23046148, compound

HRID 2107631Notes

Reaction equation

HRID 2107631 reaction equation
[C:1]([C:6]1[C:7](Cl)=[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].[NH2:16][C:17]1[C:18]([CH3:23])=[CH:19][CH:20]=[CH:21][CH:22]=1>O1CCOCC1.ClCCl>[C:1]([C:6]1[C:7]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])=[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

5

Reactant 2

HCID 7242O-ToluidineHCID 23046142HCID 23046142, compound

Product 1

HCID 23046148HCID 23046148, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

6-Butyryl-7-chlorothieno[3,2-b]pyridine (2.5 g, 0.0104 mol) and o-toluidine (2.23 g, 0,0208 mol) in 1,4-dioxan were heated under reflux for 3 hours. The solvent was evaporated under reduced pressure and the residue obtained was dissolved in dichloromethane (100 ml) and washed with 2NHCl (4×100 ml), then sodium carbonate solution (100 ml). The dichloromethane extracts were dried, filtered and evaporated under reduced pressure to give an oil, which crystallized on the addition of petroleum ether (b.p. 40°-60°). The solid was collected by filtration and dried to give 6-butyryl-7-(2-methylphenylamino)thieno[3,2-b]pyridine, (2.25 g), m.p. 114°-116°. 1 g was recrystallized from hexane to give an analytically pure sample, (0.7 g), m.p. 118°-120°.

Workup

  1. temperatureunder reflux for 3 hours
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue obtained
  4. washwashed with 2NHCl (4×100 ml)
  5. dry with materialThe dichloromethane extracts were dried
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customto give an oil, which
  9. customcrystallized on the addition of petroleum ether (b.p. 40°-60°)
  10. filtrationThe solid was collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-e54ddcbb159840a2ac099f5cafb0f035
Source dataset
uspto-grants-1990_06
Patent number
US04935431

Reaction notes

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