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 363178Notes

Reaction equation

HRID 363178 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 100° 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-1db49a817be94af9bf948d8ec3176662
Source dataset
uspto-grants-1999_02
Patent number
US05872253

Reaction notes

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