Pyridine → 5-Bromoisatoic Anhydride

HRID 1783630Notes

Reaction equation

HRID 1783630 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Br: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>[Br: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 798582-Amino-5-bromobenzoic acidHCID 94429Triphosgene

Product 1

HCID 2885615-Bromoisatoic AnhydrideYield 277.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-amino-5-bromo-benzoic acid (270 g, 1.25 mol) in acetonitrile (1250 mL) was added a solution of triphosgene (123.8 g, 416.7 mmol) in dichloromethane (DCM) (500 mL) and pyridine (197.5 g, 2.5 mol) simultaneously at 55° C. The resultant mixture was stirred for another 3 hours then cooled to room temperature. The precipitate was collected by filtration, washed with acetonitrile and dried to afford 6-bromo-1H-benzo[d][1,3]oxazine-2,4-dione as a pale powder (280 g, 93%). 1H NMR (DMSO-d6): δ 11.83 (s, 1H), 7.98 (s, 1H), 7.89-7.87 (d, 1H,), 7.09-7.07 (d, 1H).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with acetonitrile
  3. customdried

Sources & evidence

ORD record
ord-6119456a886f44c8a859bfe7ffa6b0aa
Source dataset
uspto-grants-2009_03
Patent number
US07501428B2

Reaction notes

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