Potassium Carbonate → HCID 18320746, compound

HRID 1699532Notes

Reaction equation

HRID 1699532 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]([C:13]#[N:14])=[C:11]([C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]([CH3:24])[CH:16]=2)[N:10]([C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[NH:27][CH:26]=2)[C:9]1=[O:34])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:42][CH2:43][CH2:44][N:45]1[C:49](=[O:50])[C:48]2=[CH:51][CH:52]=[CH:53][CH:54]=[C:47]2[C:46]1=[O:55]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[C:12]([C:13]#[N:14])=[C:11]([C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]([CH3:24])[CH:16]=2)[N:10]([C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]([CH2:42][CH2:43][CH2:44][N:45]3[C:49](=[O:50])[C:48]4[C:47](=[CH:54][CH:53]=[CH:52][CH:51]=4)[C:46]3=[O:55])[CH:26]=2)[C:9]1=[O:34])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 18320684HCID 18320684, compound

Product 1

HCID 18320746HCID 18320746, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 0.12 g (0.28 mmol) of the product from step c) and 0.15 g (1.1 mmol) of K2CO3 in dry 5 ml of DMF was added 0.083 g (0.30 mmol) of N-(3-bromopropyl)-phthalimide. The mixture was stirred at room temperature overnight and then partitioned between water and ethyl acetate. The aqueous phase was extracted with ethyl acetate and the combined organic phases were washed with water, brine, dried over Na2SO4 and evaporated. Chromatography on SiO2 (heptan-ethyl acetate) gave the title compound (152 mg, 86%).

Workup

  1. custompartitioned between water and ethyl acetate
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. washthe combined organic phases were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-cdbfd6d147d14afe9346671e6d476157
Source dataset
uspto-grants-2002_02
Patent number
US06346625B1

Reaction notes

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