Water → 3-phthalimido-2,3-dihydro-1,5-benzoxazepin-4(5H)-one

HRID 1632772Notes

Reaction equation

HRID 1632772 reaction equation
Cl[CH:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[O:4][CH2:3]1.[C:14]1(=[O:24])[NH:18][C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12.[K].O>CN(C)C=O>[C:14]1(=[O:24])[N:18]([CH:2]2[C:8](=[O:9])[NH:7][C:6]3[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=3[O:4][CH2:3]2)[C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12

Participants

5

Reactant 3

HCID 962WaterHCID 133751563-chloro-2,3-dihydro-1,5-benzoxazepin-4(5H)-oneHCID 24194345Phthalimide potassium salt

Product 1

HCID 133751583-phthalimido-2,3-dihydro-1,5-benzoxazepin-4(5H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.989 g of 3-chloro-2,3-dihydro-1,5-benzoxazepin-4(5H)-one and 1.0 g of potassium phthalimide in 5 ml of dimethylformamide is warmed to 90° overnight. The reaction mixture is poured into 20 ml of water and stirring is continued for 1 hr. Isolation by vacuum filtration and drying at 60° in vacuo affords 3-phthalimido-2,3-dihydro-1,5-benzoxazepin-4(5H)-one; m.p. 188°-193°; NMR (DMSO, d6) δ 7.95 (s, 4), 6.61-7.40 (m, 5), 4.92 (d of d, 1), 4.01 (d, 2).

Workup

  1. temperatureis warmed to 90° overnight
  2. filtrationIsolation by vacuum filtration
  3. customdrying at 60° in vacuo

Sources & evidence

ORD record
ord-94a31c0a37b14ddfafba65762e83e19d
Source dataset
uspto-grants-1984_10
Patent number
US04477464

Reaction notes

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