Hydrochloric Acid → 6-Acetamido-(2,6-difluoro-phenyl)-benzo[d][1,3]oxazin-4-one

HRID 567676

Reaction equation

HRID 567676 reaction equation
[C:1]([NH:4][C:5]1[CH:13]=[C:9]([C:10]([OH:12])=[O:11])[C:8]([NH2:14])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[F:15][C:16]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:17]=1[C:18](Cl)=O.FC1C=CC=C(F)C=1C1OC(=O)C2C=C([N+]([O-])=O)C=CC=2N=1.Cl>C(N(CC)CC)C.C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]2[N:14]=[C:18]([C:17]3[C:16]([F:15])=[CH:24][CH:23]=[CH:22][C:21]=3[F:25])[O:11][C:10](=[O:12])[C:9]=2[CH:13]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 874382,6-Difluorobenzoyl chlorideHCID 170890Benzoic acid, 5-(acetylamino)-2-amino-HCID 212624642-(2,6-Difluoro-phenyl)-6-nitro-benzo[d][1,3]oxazin-4-one

Product 1

HCID 99488136-Acetamido-(2,6-difluoro-phenyl)-benzo[d][1,3]oxazin-4-oneYield 94%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 22504574Toluene triethylamineSolvent

Procedure

5-Acetamidoanthranilic acid (0.64g) and 2,6-difluorobenzoyl chloride (1.3 g) were reacted in triethyl amine/toluene (1/1) (20 mL) like described for compound (9), reaction time 1 h. Ethyl acetate (50 mL) and HCl-solution (1 mL 4N in 50 mL water) were added resulting in the formation of a precipitate.The mixture was filtered and the residue dissolved in THF followed by evaporation to dryness, subsequent dissolution in hot dioxane followed by precipitation with hexane resulted in colourless crystals of 6-acetamido-(2,6-difluoro-phenyl)-benzo[d][1,3]oxazin-4-one (0.98 g), mp.246 C, MS m/e.: 316 M+.

Workup

  1. customresulting in the formation of a precipitate.The mixture
  2. filtrationwas filtered
  3. dissolutionthe residue dissolved in THF
  4. customfollowed by evaporation to dryness, subsequent dissolution in hot dioxane
  5. customfollowed by precipitation with hexane

Sources & evidence

ORD record
ord-3e485fe52fe24eaab6bc8b1cb4ca842a
Source dataset
uspto-grants-2001_01
Patent number
US06180625B2

Linked notes

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