Water → N-[5-fluoro-1-(o-methoxyphenyl)-1H-benzotriazol-6-yl]-1-cyclohexene-1,2-dicarboximide

HRID 1078014Notes

Reaction equation

HRID 1078014 reaction equation
[NH2:1][C:2]1[C:3]([F:19])=[CH:4][C:5]2[N:9]=[N:8][N:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[O:16][CH3:17])[C:6]=2[CH:18]=1.[C:20]1(=O)[O:25][C:23](=[O:24])[C:22]2[CH2:26][CH2:27][CH2:28][CH2:29][C:21]1=2.O.C(OCC)(=O)C>C(O)(=O)C.C(Cl)Cl>[F:19][C:3]1[C:2]([N:1]2[C:20](=[O:25])[C:21]3[CH2:29][CH2:28][CH2:27][CH2:26][C:22]=3[C:23]2=[O:24])=[CH:18][C:6]2[N:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[O:16][CH3:17])[N:8]=[N:9][C:5]=2[CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 153460676-Amino-5-fluoro-1-(o-methoxyphenyl)-1H-benzotriazole

Product 1

HCID 15346068N-[5-fluoro-1-(o-methoxyphenyl)-1H-benzotriazol-6-yl]-1-cyclohexene-1,2-dicarboximide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 6-amino-5-fluoro-1-(o-methoxyphenyl)-1H-benzotriazole (5.10 g, 0.019 mol) and 3,4,5,6-tetrahydrophthalic anhydride (3.68 g, 0.024 mol) in acetic acid is refluxed for 6 hours, cooled to room temperature and poured into water. The resultant aqueous mixture is extracted with ethyl acetate. The organic extracts are combined, washed sequentially with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain an orange oil. Flash column chromatography of the oil using silica gel and 2.5% to 5% ethyl acetate in methylene chloride solutions gives the title product as an orange solid, mp 83°-87° C.

Workup

  1. extractionThe resultant aqueous mixture is extracted with ethyl acetate
  2. washwashed sequentially with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain an orange oil

Sources & evidence

ORD record
ord-6c17e9a1f1284ff094d3a1338f4e44e3
Source dataset
uspto-grants-1996_08
Patent number
US05545742

Reaction notes

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