Sodium Cyanate → 4-Bromoisatoic anhydride

HRID 2274137Notes

Reaction equation

HRID 2274137 reaction equation
[O-:1]C#N.[Na+].[NH2:5][C:6]1[CH:15]=[C:14]([Br:16])[CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9]>C(O)(=O)C.O>[Br:16][C:14]1[CH:13]=[CH:12][C:7]2[C:8](=[O:9])[O:10][C:11](=[O:1])[NH:5][C:6]=2[CH:15]=1

Participants

5

Reactant 2

HCID 517096Sodium CyanateHCID 17871390Methyl 2-Amino-4-bromobenzoate

Product 1

HCID 115215774-Bromoisatoic anhydrideYield 72.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

87.0 g (1.33 mol) of sodium cyanate were added to 269.0 g (1.17 mol) of methyl 2-amino-4-bromobenzoate in 1.2 l of acetic acid with stirring at room temperature, and the mixture was subsequently stirred for a further 22 h. The reaction mixture was diluted with 1.5 l of water, and the residue was filtered off with suction. 0.42 l of sodium hydroxide solution (32%) was added to the solid, the mixture was diluted with 3.5 l of water and heated on a steam bath for 4 h. After cooling, the solid residue was filtered off with suction. Conventional work-up gave 205.2 g of 7-bromo-1H-benzo[d]-1,3-oxazine-2,4-dione; HPLC/MS (M+H)+=243 as solid.

Workup

  1. stirringthe mixture was subsequently stirred for a further 22 h
  2. filtrationthe residue was filtered off with suction
  3. addition0.42 l of sodium hydroxide solution (32%) was added to the solid
  4. additionthe mixture was diluted with 3.5 l of water
  5. temperatureheated on a steam bath for 4 h
  6. temperatureAfter cooling
  7. filtrationthe solid residue was filtered off with suction

Sources & evidence

ORD record
ord-f226577ad06444f0977e6ba37ed9c030
Source dataset
uspto-grants-2015_09
Patent number
US09126952B2

Reaction notes

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