Ethyl Acetate → N-{4-Chloro-2-fluoro-5-[hexahydro-2,4,6,-trioxo-3-(2-propynyl)-s-triazin-1-yl]phenyl}-1-cyclohexene-1,2-dicarboximide

HRID 975776Notes

Reaction equation

HRID 975776 reaction equation
[NH2:1][C:2]1[C:3]([F:21])=[CH:4][C:5]([Cl:20])=[C:6]([N:8]2[C:13](=[O:14])[NH:12][C:11](=[O:15])[N:10]([CH2:16][C:17]#[CH:18])[C:9]2=[O:19])[CH:7]=1.[C:22]1(=O)[O:27][C:25](=[O:26])[C:24]2[CH2:28][CH2:29][CH2:30][CH2:31][C:23]1=2.C(OCC)(=O)C>C(O)(=O)C>[Cl:20][C:5]1[C:6]([N:8]2[C:13](=[O:14])[NH:12][C:11](=[O:15])[N:10]([CH2:16][C:17]#[CH:18])[C:9]2=[O:19])=[CH:7][C:2]([N:1]2[C:22](=[O:27])[C:23]3[CH2:31][CH2:30][CH2:29][CH2:28][C:24]=3[C:25]2=[O:26])=[C:3]([F:21])[CH:4]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 196907381-(5-Amino-2-chloro-4-fluorophenyl)-3-(2-propynyl)-s-triazine-2,4,6-(1H,3H,5H)-trione

Product 1

HCID 131719897N-{4-Chloro-2-fluoro-5-[hexahydro-2,4,6,-trioxo-3-(2-propynyl)-s-triazin-1-yl]phenyl}-1-cyclohexene-1,2-dicarboximideYield 55.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1-(5-amino-2-chloro-4-fluorophenyl)-3-(2-propynyl)-s-triazine-2,4,6-(1H,3H,5H)-trione (1.50 g, 4.83 mmol), and 3,4,5,6-tetrahydrophthalic anhydride (0.73 g, 4.83 mmol) in acetic acid (3 mL) is heated at 0° C. for 5 hours, cooled, and poured into ethyl acetate. The organic mixture is washed sequentially with water, saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a yellow semi-solid. Flash column chromatography of the semi-solid using silica gel and an ethyl acetate/hexanes (1:2) solution gives the title product as a white solid (1.20 g, mp 127°-135° C.).

Workup

  1. temperaturecooled
  2. washThe organic mixture is washed sequentially with water, saturated sodium hydrogen carbonate solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain a yellow semi-solid

Sources & evidence

ORD record
ord-d28a9aed723a4161a18fc3df5ba16ae3
Source dataset
uspto-grants-1997_03
Patent number
US05610120

Reaction notes

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