Acetic Anhydride → 7-Chloro-3-(5-methyl-1,2,4-oxadiazol-3-yl)-5,6-dihydro-6-oxo-4H-imidazo[1,5-a][4,1]benzoxazepine

HRID 1110936Notes

Reaction equation

HRID 1110936 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:21](OC(=O)C)(=O)[CH3:22]>>[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:21]([CH3:22])[O:19][N:18]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 537468867-Chloro-5,6-dihydro-6-oxo-4H-imidazo[1,5-a]-[4,1]benzoxazepine-3-amidoxime

Product 1

HCID 538821017-Chloro-3-(5-methyl-1,2,4-oxadiazol-3-yl)-5,6-dihydro-6-oxo-4H-imidazo[1,5-a][4,1]benzoxazepineYield 66%

Procedure

7-Chloro-5,6-dihydro-6-oxo-4H-imidazo[1,5-a]-[4,1]benzoxazepine-3-amidoxime (3 g, 0.01 mole) in acetic anhydride (9 ml) was heated at 150° C. for 3 hours. The crude product in ethyl acetate was chromatographed on silica and then crystallised from acetone to give the product (2.1 g, 66%), m.p. 253°-255° C.

Workup

  1. customThe crude product in ethyl acetate was chromatographed on silica
  2. customcrystallised from acetone

Sources & evidence

ORD record
ord-00d4fde57e9e4b2bbebdbdd47fe5a605
Source dataset
uspto-grants-1990_12
Patent number
US04977258

Reaction notes

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