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

HRID 1110937Notes

Reaction equation

HRID 1110937 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)CCC)(=O)CCC>[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:7]([CH2:2][CH2:3][CH3:4])[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 540796957-Chloro-3-(5-propyl-1,2,4-oxadiazol-3-yl)-5,6-dihydro-6-oxo-4H-imidazo[1,5-a][4,1]benzoxazepineYield 99.5%

Reagents, catalysts & solvents 1

HCID 7798Butyric anhydrideSolvent

Procedure

7-Chloro-5,6-dihydro-6-oxo-4H-imidazo[1,5-a]-[4,1]benzoxazepine-3-amidoxime (2 g, 7 mmole) in n-butyric anhydride (6 ml) was heated at 150° C. for 1 hour. The crude product was chromatographed on silica, initially with ethyl acetate:hexane (1:1) and then changing to ethyl acetate. The purified product was crystallised from ethyl acetate:cyclohexane (4:1) to give the product (1.2 g, 50%), m.p. 130°-132° C.

Workup

  1. customThe crude product was chromatographed on silica, initially with ethyl acetate:hexane (1:1)
  2. customThe purified product was crystallised from ethyl acetate:cyclohexane (4:1)

Sources & evidence

ORD record
ord-aa1ca97b95f6411d9789bf38761b10d1
Source dataset
uspto-grants-1990_12
Patent number
US04977258

Reaction notes

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