Methyl Isocyanate → 1-(1-Bromo-3-isopropyl-4-oxo-3,4-dihydro-phthalazin-6-yl)-3-methyl-urea

HRID 1765351Notes

Reaction equation

HRID 1765351 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([Br:16])=[N:7][N:8]([CH:13]([CH3:15])[CH3:14])[C:9]2=[O:12])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:19][N:20]=[C:21]=[O:22]>O1CCCC1>[Br:16][C:6]1[C:5]2[C:10](=[CH:11][C:2]([NH:1][C:21]([NH:20][CH3:19])=[O:22])=[CH:3][CH:4]=2)[C:9](=[O:12])[N:8]([CH:13]([CH3:14])[CH3:15])[N:7]=1

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 24758Sodium hydrideHCID 211065807-Amino-2-Isopropyl-4-bromo-2H-phthalazin-1-one

Product 1

HCID 211065081-(1-Bromo-3-isopropyl-4-oxo-3,4-dihydro-phthalazin-6-yl)-3-methyl-ureaYield 78.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

7-Amino-2-Isopropyl-4-bromo-2H-phthalazin-1-one (0.5 g, 1.77 mmol) was dissolved in tetrahydrofuran (THF) (5 ml). To this was added NaH (60%, 0.14 g, 3.54 mmol) as a suspension in THF (2 ml) and the reaction mixture was stirred for 5 minutes. After this time methyl isocyanate (0.2 g, 3.55 mmol) was added in one portion and the reaction mixture was stirred at room temperature for a further 48 hours. After this time, the reaction mixture was partitioned between ethyl acetate (50 ml) and water (50 ml), the organic layer was separated, dried (MgSO4), filtered and concentrated under vacuum to give the title compound (0.47 g, 78% yield) as a light brown solid.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for a further 48 hours
  2. customAfter this time, the reaction mixture was partitioned between ethyl acetate (50 ml) and water (50 ml)
  3. customthe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a391947cd6f24502bbd47efe48fab498
Source dataset
uspto-grants-2007_06
Patent number
US07226923B2

Reaction notes

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