Reaction #361729

ord-23d58143224d4d4fa38511ce9689b20b

Reaction equation

COc1cc(C(=O)n2ccnc2)cc([N+](=O)[O-])c1OC
1-(3,4-dimethoxy-5-nitrobenzoyl)imidazole
CC(N)=NO
acetamidoxime
→
COc1cc(C(=O)ON=C(C)N)cc([N+](=O)[O-])c1OC
N'-[(3,4-dimethoxy-5-nitrobenzoyl)oxy]acetamidine

Reactants

—
ice water
COc1cc(C(=O)n2ccnc2)cc([N+](=O)[O-])c1OC
1-(3,4-dimethoxy-5-nitrobenzoyl)imidazole
CC(N)=NO
acetamidoxime

Reagents

None

Solvents

CN(C)C=O
dimethylformamide

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureAfter cooling
  2. 2
    workup.STIRRINGstirred for 30 minutes
  3. 3
    FiltrationThe separated crystals are filtered under suction
  4. 4
    Washwashed with water
  5. 5
    OtherAfter crystallization from ethyl acetate

Procedure

10.0 g of 1-(3,4-dimethoxy-5-nitrobenzoyl)imidazole in 50 ml of dimethylformamide are treated with 6.95 g of acetamidoxime, whereupon the mixture is stirred at 70° for 1 hour. After cooling, the mixture is poured into 500 ml of ice-water and stirred for 30 minutes. The separated crystals are filtered under suction and washed with water. After crystallization from ethyl acetate there is obtained N'-[(3,4-dimethoxy-5-nitrobenzoyl)oxy]acetamidine in the form of colorless crystals of m.p. 165°-166°.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05389653uspto-grants-1995_02