Thiourea → HCID 178527723, compound

HRID 1581499Notes

Reaction equation

HRID 1581499 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-f73fc87cc6944b32923d3fc8c41278cd
Source dataset
uspto-grants-2004_05
Patent number
US06730674B2

Reaction notes

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