Phenacyl bromide → HCID 22100363, compound

HRID 1457775Notes

Reaction equation

HRID 1457775 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[NH:12][C:11]([CH2:13][CH2:14][CH2:15][CH3:16])=[N:10][C:5]2=[N:6][C:7]=1[CH2:8][OH:9].Br[CH2:18][C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[N:12]=[C:11]([CH2:13][CH2:14][CH2:15][CH3:16])[N:10]([CH2:18][C:19](=[O:20])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:5]2=[N:6][C:7]=1[CH2:8][OH:9]

Participants

6

Reactant 3

HCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 22100389HCID 22100389, compound

Product 1

HCID 22100363HCID 22100363, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

10 g(0.0352 mole) of the compound obtained in step 6, 7.59 g(0.0387 mole) of 2-bromoacetophenone and 9.8 g(0.0704 mole) of K2CO3 were dissolved in 50 ml of dimethyl formamide. The reaction solution was stirred for 3 hours at room temperature, diluted with 200 ml of ethyl acetate and washed with water(100 ml×3). The organic layer was dried over Na2SO4 and purified with column chromatography(silica gel, methylene chloride:ethyl acetate =1:1) to obtain 6.96 g of the title compound(yield 64%).

Workup

  1. washwashed with water(100 ml×3)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. custompurified with column chromatography(silica gel, methylene chloride:ethyl acetate =1:1)

Sources & evidence

ORD record
ord-936b9a2161464a6382dee3143fcbcaa2
Source dataset
uspto-grants-1998_12
Patent number
US05849753

Reaction notes

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