Nitrogen → 2-(2,6-Difluoro-phenyl)-6-nitro-benzo[d][1,3]oxazin-4-one

HRID 567675

Reaction equation

HRID 567675 reaction equation
[N+:1]([C:4]1[CH:12]=[C:8]([C:9]([OH:11])=[O:10])[C:7]([NH2:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].[F:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:16]=1[C:17](Cl)=O.N#N>C(N(CC)CC)C.C1(C)C=CC=CC=1>[F:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:16]=1[C:17]1[O:10][C:9](=[O:11])[C:8]2[CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=2[N:13]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 120322-Amino-5-nitrobenzoic acidHCID 874382,6-Difluorobenzoyl chloride

Product 1

HCID 212624642-(2,6-Difluoro-phenyl)-6-nitro-benzo[d][1,3]oxazin-4-one

Reagents, catalysts & solvents 1

HCID 22504574Toluene triethylamineSolvent

Procedure

5-Nitroanthranilic acid (0.6 g) was dissolved in triethyl amine/toluene (1/1) (18 mL) and stirred for 10 min. 2,6-Difluorobenzoylchloride (1.3 g) was slowly added under stirring which resulted in the formation of a precipitate. The reaction was performed in an N2-atmosphere. After stirring at RT for 24 h the mixture was extracted with sat.NaHCO3 and ethyl acetate (20 mL), the organic layer was separated and evaporated.

Workup

  1. stirringunder stirring which
  2. customresulted in the formation of a precipitate
  3. stirringAfter stirring at RT for 24 h the mixture
  4. extractionwas extracted
  5. customNaHCO3 and ethyl acetate (20 mL), the organic layer was separated
  6. customevaporated

Sources & evidence

ORD record
ord-799a40c324144e02bf5f287d1693f394
Source dataset
uspto-grants-2001_01
Patent number
US06180625B2

Linked notes

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