Acetone → HCID 67496401, compound

HRID 1952541Notes

Reaction equation

HRID 1952541 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([Br:11])[C:3]=1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]CBr.[C:21]1(=[O:31])[NH:25][C:24](=[O:26])[C:23]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:22]12.[K].[CH3:33]C(C)=O>>[Br:11][C:4]1[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=[C:2]([Br:1])[C:3]=1[O:12][CH:13]([CH3:33])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][N:25]1[C:21](=[O:31])[C:22]2[C:23](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:24]1=[O:26]

Participants

4

Reactant 3

HCID 180AcetoneHCID 24194345Phthalimide potassium saltHCID 67495855HCID 67495855, compound

Product 1

HCID 67496401HCID 67496401, compound

Procedure

To a solution of 11 (1.33 g, 2.34 mmol) in acetone (30 mL) was added potassium phthalimide (0.56 g, 3.05 mmol). The resulting mixture was stirred for 24 hours under reflux conditions. The reaction mixture was cooled to room temperature and filtered through Celite. The filtrate was concentrated in vacuo. MPLC purification (Hexanes:EtOAc/80:20) of the residue gave 12 as a white amorphous solid (1.18 g, 80%). 1H NMR (CDCl3) δ 8.63 (s, 2H), 7.83-7.85 (m, 2H), 7.70-7.72 (m, 2H), 4.02 (t, J=6.4 Hz, 2H), 3.70 (t, J=7.2 Hz, 2H), 1.91-1.95 (m, 2H), 1.69-1.73 (m, 2H), 1.55-1.58 (m, 2H), and 1.40-1.46 (m, 2H).

Workup

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. customMPLC purification (Hexanes:EtOAc/80:20) of the residue

Sources & evidence

ORD record
ord-333f20f001024b3180d0d4a0fe5c7901
Source dataset
uspto-grants-2013_03
Patent number
US08404728B2

Reaction notes

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