Thiourea → HCID 178527723, compound

HRID 22761Notes

Reaction equation

HRID 22761 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 15.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 3-benzyloxy-6-chloro-pyridazine (18.2 mmol, 4 g), thiourea (36.3 mmol, 2.8 g) and ethyl methyl ketone (75 mL) was refluxed overnight. Excess ethyl methyl ketone was evaporated, the residue was extracted with 2M sodium hydroxide (25 mL) and the sodium hydroxide solution was washed with EtOAc (2×30 mL). The aqueous layer was collected and sufficient conc. HCl was added to bring the pH to 5 and extracted with EtOAc (2×30 mL). The EtOAc extract was collected, dried, filtered and the filtrate was evaporated to yield 3-benzyloxy-6-mercapto-pyridazine (15%, 605 mg); mp 155° C.-157° C.

Workup

  1. temperaturewas refluxed overnight
  2. customExcess ethyl methyl ketone was evaporated
  3. extractionthe residue was extracted with 2M sodium hydroxide (25 mL)
  4. washthe sodium hydroxide solution was washed with EtOAc (2×30 mL)
  5. customThe aqueous layer was collected
  6. additionsufficient conc. HCl was added
  7. extractionextracted with EtOAc (2×30 mL)
  8. extractionThe EtOAc extract
  9. customwas collected
  10. customdried
  11. filtrationfiltered
  12. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-df9c3c46233e4d73b1173ac3874fed00
Source dataset
uspto-grants-2005_02
Patent number
US06849629B2

Reaction notes

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