Bis(2-chloroethyl) ether → HCID 21106586, compound

HRID 1783658Notes

Reaction equation

HRID 1783658 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.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:24][CH2:25][O:26][CH2:27][CH2:28]Cl>CN(C=O)C>[O:26]1[CH2:27][CH2:28][N:1]([C:2]2[CH:11]=[C:10]3[C:5]([C:6]([Br:16])=[N:7][N:8]([CH:13]([CH3:14])[CH3:15])[C:9]3=[O:12])=[CH:4][CH:3]=2)[CH2:24][CH2:25]1

Participants

5

Reactant 3

HCID 8115Bis(2-chloroethyl) etherHCID 11430Potassium CarbonateHCID 211065807-Amino-2-Isopropyl-4-bromo-2H-phthalazin-1-one

Product 1

HCID 21106586HCID 21106586, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 7-Amino-2-Isopropyl-4-bromo-2H-phthalazin-1-one (0.8 g, 0.0028 mol) in DMF (8 ml), was added potassium carbonate (2 g, 0.014 mol). After 5 min, bis (2-chloroethyl) ether (0.41 g, 0.0028 mol) was added and the solution was heated to 140° C. for 24 hours. After this time LC-MS indicated the complete consumption of starting material and the mixture was cooled, concentrated under vacuum and purified by flash column chromatography (elution: 70% heptane, 30% EtOAc) to give the title compound (0.2 g, 20% yield) as a white solid.

Workup

  1. customthe complete consumption of starting material
  2. temperaturethe mixture was cooled
  3. concentrationconcentrated under vacuum
  4. custompurified by flash column chromatography (elution: 70% heptane, 30% EtOAc)

Sources & evidence

ORD record
ord-44cb8c55a5864b4ba8165ac3f64e8624
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

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