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

HRID 1783665Notes

Reaction equation

HRID 1783665 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]>C1COCC1>[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 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 min. After this time methyl isocyanate (0.2 g, 3.55 mmol) was added in one portion and the reaction mixture was stirred at RT for a further 48 hours. After this time, the reaction mixture was partitioned between EtOAc (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 RT for a further 48 hours
  2. customAfter this time, the reaction mixture was partitioned between EtOAc (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-c7043891c3154eb2a99d8c1382fa8984
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

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