4-Bromophenacyl bromide → HCID 18545776, compound

HRID 1533170Notes

Reaction equation

HRID 1533170 reaction equation
[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([NH:7][CH2:8][C:9](=[O:13])[NH:10]2)=[CH:5][CH:4]=1)#[N:2].C([O-])([O-])=O.[K+].[K+].C1OCCOCCOCCOCCOCCOC1.Br[CH2:39][C:40]([C:42]1[CH:47]=[CH:46][C:45]([Br:48])=[CH:44][CH:43]=1)=[O:41]>C1COCC1.CCOC(C)=O>[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([NH:7][CH2:8][C:9](=[O:13])[N:10]2[CH2:39][C:40]([C:42]2[CH:47]=[CH:46][C:45]([Br:48])=[CH:44][CH:43]=2)=[O:41])=[CH:5][CH:4]=1)#[N:2]

Participants

7

Reactant 4

HCID 74544-Bromophenacyl bromideHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 107973017-cyano-3,4-dihydroquinoxalin-2(1H)-one

Product 1

HCID 18545776HCID 18545776, compoundYield 37.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-cyano-3,4-dihydroquinoxalin-2(1H)-one (4 mg, 20 mmol) in THF (100 mL) was added K2CO3 (152 mg, 1.1 mmoL), 18-crown-6 (230 mg), and 2,4′-dibromoacetophenone (5.54 g, 20 mmol), and the resulting mixture was stirred for 16 hours. The mixture was diluted with EtOAc and filtered. The residue was washed with EtOAc and water, and dried by air to give the product (2.8 g, 37.8%). The filtrate was washed with brine (50 mL×4), dried over MgSO4, and concentrated to give a crude material, which was recrystallized in EtOAc (20 mL) to give the product (2 g, 27%) as a white solid. 1H NMR (DMSO-d6) δ 8.02 (d, J=8.4 Hz, 2H), 7.83 (d, J=8.4 Hz, 2H), 7.35 (d, J=1.4 Hz, 1H), 7.26 (dd, J=8.1 Hz, J=1.4 Hz, 1H), 7.10 (s, 1H), 6.81 (d, J=8.4 Hz, 1H), 5.50 (s, 2H), 4.05 (d, J=1.1 Hz, 2H); MS(CI) m/z 370/372 (M+H).

Workup

  1. filtrationfiltered
  2. washThe residue was washed with EtOAc and water
  3. customdried by air

Sources & evidence

ORD record
ord-a4ec649b9d694fd29b2b69141b67795a
Source dataset
uspto-grants-2001_03
Patent number
US06207697B1

Reaction notes

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