Propargyl bromide → N-{5-[3-Allylhexahydro-2,4,6-trioxo-5-(2-propynyl)-s-triazin-1-yl]-4-chloro-2-fluorophenyl}-1-cyclohexene-1,2-dicarboximide

HRID 725243Notes

Reaction equation

HRID 725243 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[CH2:5]([N:8]1[C:13](=[O:14])[NH:12][C:11](=[O:15])[N:10]([C:16]2[C:17]([Cl:34])=[CH:18][C:19]([F:33])=[C:20]([N:22]3[C:31](=[O:32])[C:26]4[CH2:27][CH2:28][CH2:29][CH2:30][C:25]=4[C:23]3=[O:24])[CH:21]=2)[C:9]1=[O:35])[CH:6]=[CH2:7].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[CH2:1]([N:12]1[C:13](=[O:14])[N:8]([CH2:5][C:6]#[CH:7])[C:9](=[O:35])[N:10]([C:16]2[C:17]([Cl:34])=[CH:18][C:19]([F:33])=[C:20]([N:22]3[C:31](=[O:32])[C:26]4[CH2:27][CH2:28][CH2:29][CH2:30][C:25]=4[C:23]3=[O:24])[CH:21]=2)[C:11]1=[O:15])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 7842Propargyl bromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 86750499N-[5-(3-allylhexahydro-2,4,6-trioxo-s-triazin-1-yl)-4-chloro-2-fluorophenyl]-1-cyclohexene-1,2-dicarboximide

Product 1

HCID 86750498N-{5-[3-Allylhexahydro-2,4,6-trioxo-5-(2-propynyl)-s-triazin-1-yl]-4-chloro-2-fluorophenyl}-1-cyclohexene-1,2-dicarboximideYield 55.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Propargyl bromide (0.37 mL, 3.36 mmol) is added to a mixture of N-[5-(3-allylhexahydro-2,4,6-trioxo-s-triazin-1-yl)-4-chloro-2-fluorophenyl]-1-cyclohexene-1,2-dicarboximide (1.00 g, 2.24 mmol), and potassium carbonate (0.62 g, 4.48 mmol) in N,N-dimethylformamide. The reaction mixture is stirred for 7 hours, and poured into ethyl acetate. The organic solution is washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a yellow oil. Flash column chromatography of the oil using silica gel and an ethyl acetate/hexanes (1:4) solution gives the title product as a white solid (0.60 g, mp 107°-114° C.).

Workup

  1. washThe organic solution is washed sequentially with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto obtain a yellow oil

Sources & evidence

ORD record
ord-6b2e7d70187a4ceb8e97fa0924c281e6
Source dataset
uspto-grants-1998_01
Patent number
US05705644

Reaction notes

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