Thiourea → HCID 178527723, compound

HRID 985409Notes

Reaction equation

HRID 985409 reaction equation
[CH2:1]([O:8][C:9]1[N:10]=[N:11][C:12](Cl)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NC(N)=[S:18]>CC(CC)=O>[CH2:1]([O:8][C:9]1[N:10]=[N:11][C:12]([SH:18])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 225069573-(Benzyloxy)-6-chloropyridazine

Product 1

HCID 178527723HCID 178527723, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 3-benzyloxy-6-chloro-pyridazine (4 g), thiourea (2.8 g) and ethyl methyl ketone (75 mL) was prepared and refluxed overnight. Excess ethyl methyl ketone was evaporated and the resulting residue was extracted with 2M sodium hydroxide (25 mL). The sodium hydroxide solution was then washed with ethyl acetate (2×30 mL). The aqueous layer was collected and sufficient concentrated hydrochloric acid was added to bring the pH to 5. The resulting solution was extracted with ethyl acetate (2×30 mL). The ethyl acetate extract was collected, dried, filtered, and the filtrate was evaporated to afford the title compound (15%, 605 mg); mp, 155-157° C.

Workup

  1. customwas prepared
  2. temperaturerefluxed overnight
  3. customExcess ethyl methyl ketone was evaporated
  4. extractionthe resulting residue was extracted with 2M sodium hydroxide (25 mL)
  5. washThe sodium hydroxide solution was then washed with ethyl acetate (2×30 mL)
  6. customThe aqueous layer was collected
  7. additionsufficient concentrated hydrochloric acid was added
  8. extractionThe resulting solution was extracted with ethyl acetate (2×30 mL)
  9. extractionThe ethyl acetate extract
  10. customwas collected
  11. customdried
  12. filtrationfiltered
  13. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-2e6243a7e8ed438ba4fc2581eb4c0a9b
Source dataset
uspto-grants-2005_03
Patent number
US06872722B2

Reaction notes

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