2H-3,1-Benzoxazine-2,4(1H)-dione, 6-nitro- → 2-Amino-N-[(2-chlorophenyl)methyl]-5-nitrobenzamide

HRID 1934720Notes

Reaction equation

HRID 1934720 reaction equation
[N+:1]([C:4]1[CH:15]=[C:8]2[C:9]([O:11]C(=O)[NH:13][C:7]2=[CH:6][CH:5]=1)=O)([O-:3])=[O:2].[Cl:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19][NH2:20]>CN(C)C=O>[NH2:13][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:15][C:8]=1[C:9]([NH:20][CH2:19][C:18]1[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=1[Cl:16])=[O:11]

Participants

4

Reactant 2

HCID 208212H-3,1-Benzoxazine-2,4(1H)-dione, 6-nitro-HCID 666482-Chlorobenzylamine

Product 1

HCID 224675962-Amino-N-[(2-chlorophenyl)methyl]-5-nitrobenzamideYield 90.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 5-nitroisatoic anhydride (300 mg) in dimethylformamide (4 mL) was added 2-chlorobenzylamine (245 mg), and the mixture was stirred for 15 hours at ambient temperature. The mixture was partitioned between ethyl acetate and water. The separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with diisopropyl ether to give 2-amino-N-(2-chlorobenzyl)-5-nitrobenzamide as yellow powders (397 mg).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe separated organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-ec6bb8be21c24d209b264abd9238775d
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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