Sodium ethanethiolate → 6-Bromo-1-(ethylthio)phthalazine

HRID 2357611Notes

Reaction equation

HRID 2357611 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](Cl)=[N:7][N:6]=[CH:5]2.[CH2:13]([S-:15])[CH3:14].[Na+]>C(#N)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([S:15][CH2:13][CH3:14])=[N:7][N:6]=[CH:5]2

Participants

5

Reactant 2

HCID 4459711Sodium ethanethiolateHCID 220304246-Bromo-1-chlorophthalazine

Product 1

HCID 684548926-Bromo-1-(ethylthio)phthalazine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-bromo-1-chlorophthalazine (0.22 g, 0.9 mmol) in acetonitile (5 mL) stirred at ambient was added sodium ethanethiolate (0.2 g, 2 mmol), and the mixture was stirred for 1 h. The mixture was diluted with ethyl acetate (100 mL), washed with sat. NH4Cl, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The crude product was purified by chromatography eluting with 1-5% 2 M ammonia methanol/dichloromethane to give the 6-bromo-1-(ethylthio)phthalazine as pale yellow solid.

Workup

  1. washwashed with sat. NH4Cl
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by chromatography
  5. washeluting with 1-5% 2 M ammonia methanol/dichloromethane

Sources & evidence

ORD record
ord-c43d21b735444732a9406ca5ede64749
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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