2-Amino-6-chlorobenzoic acid → 5-Chloro-2-(2,6-difluoro-phenyl)-benzo[d][1,3]oxazin-4-one

HRID 567679

Reaction equation

HRID 567679 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([NH2:11])[C:7]=1[C:8]([OH:10])=[O:9].[F:12][C:13]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:14]=1[C:15](Cl)=O.C(NC1C=CC2N=C(C3C(F)=CC=CC=3F)OC(=O)C=2C=1)(=O)C>C(N(CC)CC)C.C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]2[C:8](=[O:10])[O:9][C:15]([C:14]3[C:13]([F:12])=[CH:21][CH:20]=[CH:19][C:18]=3[F:22])=[N:11][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 750712-Amino-6-chlorobenzoic acidHCID 874382,6-Difluorobenzoyl chlorideHCID 99488136-Acetamido-(2,6-difluoro-phenyl)-benzo[d][1,3]oxazin-4-one

Product 1

HCID 212624825-Chloro-2-(2,6-difluoro-phenyl)-benzo[d][1,3]oxazin-4-one

Reagents, catalysts & solvents 1

HCID 22504574Toluene triethylamineSolvent

Procedure

6-Chloroanthranilic acid (0.566 g), 2,6-difluorobenzoyl chloride (0.93 mL) and triethyl amine/toluene (1/1) (18 mL) were reacted as described under (10). Reaction time 2 days. Extraction between ethyl acetate (100 mL) and HCl (2N, 100 mL), followed by separation of the organic layer, drylng over MgSO4, filtering and evaporation gave a crude product which was dissolved in warm THF (20 mL) and precipitated with hexane. The resulting mixture was further purified on a silicagel column using dichloromethane as eluent. The isolated fraction was dissolved in warm THF (20 mL) and precipitated with hexane, ylelding 5-chloro-2-(2,6-difluoro-phenyl)-benzo[d][1,3]oxazin-4-one (0.65 g) mp. 176 C, MS m/e: 293/295 M+.

Workup

  1. customReaction time 2 days
  2. extractionExtraction between ethyl acetate (100 mL) and HCl (2N, 100 mL)
  3. customfollowed by separation of the organic layer
  4. filtrationfiltering
  5. customevaporation

Sources & evidence

ORD record
ord-7d8dd5952bcd4302b7ea581f9731b322
Source dataset
uspto-grants-2001_01
Patent number
US06180625B2

Linked notes

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