7-Chloro-5,6-dihydro-6-oxo-4H-imidazo[1,5-a]-[4,1]benzoxazepine-3-amidoxime → 7-Chloro-3-(5-pentyl-[1,2,4]oxadiazol-3-yl)-4H-5-oxa-2,10b-diaza-benzo[e]azulen-6-one

HRID 1110938Notes

Reaction equation

HRID 1110938 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:20])[O:9][CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16](=[N:18][OH:19])[NH2:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1>C(OC(=O)CCCCC)(=O)CCCCC>[Cl:1][C:2]1[C:7]2[C:8](=[O:20])[O:9][CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[N:17]=[C:6]([CH2:7][CH2:2][CH2:3][CH2:4][CH3:5])[O:19][N:18]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 537468867-Chloro-5,6-dihydro-6-oxo-4H-imidazo[1,5-a]-[4,1]benzoxazepine-3-amidoxime

Product 1

HCID 540381147-Chloro-3-(5-pentyl-[1,2,4]oxadiazol-3-yl)-4H-5-oxa-2,10b-diaza-benzo[e]azulen-6-oneYield 122.6%

Reagents, catalysts & solvents 1

HCID 74918Hexanoic anhydrideSolvent

Procedure

7-Chloro-5,6-dihydro-6-oxo-4H-imidazo[1,5-a][4,1]benzoxazepine-3-amidoxime (2 g, 7 mmole) in caproic anhydride (8 ml) was heated at 150° C. for 30 minutes. The crude product in ethyl acetate:hexane (1:1) was chromatographed on silica to give the product (1.6 g, 63%), m.p. 110°-112° C.

Workup

  1. customThe crude product in ethyl acetate:hexane (1:1) was chromatographed on silica

Sources & evidence

ORD record
ord-b9ac31a7efb6452686b1ffcf39026447
Source dataset
uspto-grants-1990_12
Patent number
US04977258

Reaction notes

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