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

HRID 259746Notes

Reaction equation

HRID 259746 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-910edaf12e4c4a578d7133fc42f40bb8
Source dataset
uspto-grants-1996_06
Patent number
US05523277

Reaction notes

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