Sodium methanethiolate → HCID 68980262, compound

HRID 1783726Notes

Reaction equation

HRID 1783726 reaction equation
[CH3:1][S-:2].[Na+].[Br:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([CH2:15]Br)=[CH:12][CH:13]=2)[C:8](=[O:17])[N:7]([CH:18]([CH3:20])[CH3:19])[N:6]=1>C1COCC1>[Br:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([CH2:15][S:2][CH3:1])=[CH:12][CH:13]=2)[C:8](=[O:17])[N:7]([CH:18]([CH3:20])[CH3:19])[N:6]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 211065684-Bromo-7-bromomethyl-2-isopropyl-2H-phthalazin-1-one

Product 1

HCID 68980262HCID 68980262, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium methanethiolate (0.23 g, 3.33 mmol) was dissolved in THF (1 ml) and added dropwise to a solution of 4-bromo-7-bromomethyl-2-isopropyl-2H-phthalazin-1-one (0.4 g, 1.11 mmol) in THF (10 ml). The mixture was stirred at RT for 3 hours whereupon LC-MS indicated complete consumption of starting material. The reaction mixture was diluted with water (20 ml) and extracted with EtOAc (50 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated under vacuum. The residue was subjected to flash column chromatography (elution: 80% heptane, 20% EtOAc) to give the title compound (0.29 g, 79% yield) as a white solid.

Workup

  1. customconsumption of starting material
  2. additionThe reaction mixture was diluted with water (20 ml)
  3. extractionextracted with EtOAc (50 ml)
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. washThe residue was subjected to flash column chromatography (elution: 80% heptane, 20% EtOAc)

Sources & evidence

ORD record
ord-84790ff519744daea89f8d0679fadac8
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

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