2,6-Difluorobenzoyl chloride → 2-(2,6-Difluoro-phenyl)-6,7-difluoro-benzo[d][1,3]oxazin-4-one

HRID 567683

Reaction equation

HRID 567683 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[F:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:15]=1[C:16](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>[F:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:15]=1[C:16]1[O:5][C:4](=[O:6])[C:3]2[CH:7]=[C:8]([F:12])[C:9]([F:11])=[CH:10][C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 874382,6-Difluorobenzoyl chlorideHCID 7359652-Amino-4,5-difluorobenzoic acidHCID 99488136-Acetamido-(2,6-difluoro-phenyl)-benzo[d][1,3]oxazin-4-one

Product 1

HCID 98609312-(2,6-Difluoro-phenyl)-6,7-difluoro-benzo[d][1,3]oxazin-4-one

Reagents, catalysts & solvents 1

HCID 22504574Toluene triethylamineSolvent

Procedure

2-Amino-4,5-difluorobenzoic acid (0.5 g), 2,6-difluorobenzoyl chloride (0.80 mL) and triethyl amine/toluene (1/1) (18 mL) were reacted as described under (10). Reaction time 1 day. Extraction between ethyl acetate (20 mL) and HCl (2N,20 mL), followed by separation of the organic toluene and precipitated with hexane. The resulting mixture was further purified on a silicagel column using dichloromethane as eluent. The isolated fraction identified as 2-(2,6-difluoro-phenyl)-6,7-difluoro-benzo[d][1,3]oxazin-4-one (0.71 g), mp. 165 C, MS m/e: 295 M+.

Workup

  1. customReaction time 1 day
  2. extractionExtraction between ethyl acetate (20 mL) and HCl (2N,20 mL)
  3. customfollowed by separation of the organic toluene
  4. customprecipitated with hexane
  5. customThe resulting mixture was further purified on a silicagel column

Sources & evidence

ORD record
ord-a2fa7b48033c463e94febb15bcd28172
Source dataset
uspto-grants-2001_01
Patent number
US06180625B2

Linked notes

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