N-Hydroxyacetamidine → N'-[(3,4-dimethoxy-5-nitrobenzoyl)oxy]acetamidine

HRID 274547

Reaction equation

HRID 274547 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[C:14]([N+:18]([O-:20])=[O:19])[C:15]=1[O:16][CH3:17])[C:6](N1C=CN=C1)=[O:7].[C:21](=[N:24][OH:25])([NH2:23])[CH3:22]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[C:14]([N+:18]([O-:20])=[O:19])[C:15]=1[O:16][CH3:17])[C:6]([O:25][N:24]=[C:21]([NH2:23])[CH3:22])=[O:7]

Participants

4

Reactant 2

HCID 30926N-HydroxyacetamidineHCID 214590201-(3,4-Dimethoxy-5-nitrobenzoyl)imidazole

Product 1

HCID 53789064N'-[(3,4-dimethoxy-5-nitrobenzoyl)oxy]acetamidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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°.

Workup

  1. temperatureAfter cooling
  2. stirringstirred for 30 minutes
  3. filtrationThe separated crystals are filtered under suction
  4. washwashed with water
  5. customAfter crystallization from ethyl acetate

Sources & evidence

ORD record
ord-23d58143224d4d4fa38511ce9689b20b
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Linked notes

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