Pyridine → 5-Fluoroisatoic anhydride

HRID 1846282Notes

Reaction equation

HRID 1846282 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[C:13](Cl)([O:15]C(=O)OC(Cl)(Cl)Cl)Cl.N1C=CC=CC=1>C(#N)C.ClCCl>[F:11][C:8]1[CH:9]=[CH:10][C:2]2[NH:1][C:13](=[O:15])[O:5][C:4](=[O:6])[C:3]=2[CH:7]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 1014122-Amino-5-fluorobenzoic acid

Product 1

HCID 2885605-Fluoroisatoic anhydride

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 2-amino-5-fluorobenzoic acid (1.00 g, 6.40 mmol) in acetonitrile (8 mL) was added a solution of triphosgene (0.64 g, 2.1 mmol) in dichloromethane (5 mL) and pyridine (1.1 mL, 13.0 mmol) simultaneously within 5 min. The resulting pale yellow suspension was heated at 55° C. for 2 hours. The solvents were evaporated under vacuum, and the residue was stirred with water (5 mL). The precipitate obtained was filtered and dried to afford 6-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione. Yield: 1.06 g (91%).

Workup

  1. customThe solvents were evaporated under vacuum
  2. customThe precipitate obtained
  3. filtrationwas filtered
  4. customdried

Sources & evidence

ORD record
ord-5a16fceda5d84b6999f72de577d22cd0
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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