Tetrahydrofuran → (Benzo[c][1,2,5]oxadiazol-5-yl)methoxyphthalimide

HRID 41955Notes

Reaction equation

HRID 41955 reaction equation
Br[CH2:2][C:3]1[CH:11]=[CH:10][C:6]2=[N:7][O:8][N:9]=[C:5]2[CH:4]=1.O[N:13]1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23].C(N(CC)C(C)C)(C)C.[O:33]1CCCC1>>[N:7]1[O:8][N:9]=[C:5]2[CH:4]=[C:3]([CH2:2][O:33][C:19]3[CH:20]=[CH:21][CH:22]=[C:15]4[C:14]([NH:13][C:17](=[O:18])[C:16]=34)=[O:23])[CH:11]=[CH:10][C:6]=12

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 10665N-HydroxyphthalimideHCID 81531DiisopropylethylamineHCID 27355875-(Bromomethyl)-2,1,3-benzoxadiazole

Product 1

HCID 66761055(Benzo[c][1,2,5]oxadiazol-5-yl)methoxyphthalimideYield 94%

Procedure

5-(Bromomethyl)benzo[c][1,2,5]oxadiazole (0.441 g, 2.07 mmol) was added to a solution of N-hydroxyphthalimide (0.336 g, 2.06 mmol) in dry tetrahydrofuran (15 ml). N,N-Diisopropylethylamine (0.519 g, 4.02 mmol) was added and the solution was stirred at reflux under nitrogen for 23 h and cooled to room temperature. The suspension was concentrated in vacuo to a pale beige solid. This was diluted with water and filtered. The residue was washed with plenty of water and dried under vacuum to give (benzo[c][1,2,5]oxadiazol-5-yl)methoxyphthalimide (0.571 g, 94%).

Workup

  1. temperatureat reflux under nitrogen for 23 h
  2. concentrationThe suspension was concentrated in vacuo to a pale beige solid
  3. additionThis was diluted with water
  4. filtrationfiltered
  5. washThe residue was washed with plenty of water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-b1be8216ef364d1f9a71013e80cc2570
Source dataset
uspto-grants-2013_09
Patent number
US08536157B2

Reaction notes

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