Toluene → 5-chloro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

HRID 601132Notes

Reaction equation

HRID 601132 reaction equation
[OH-].[K+].[NH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:5]=1[C:6]([OH:8])=[O:7].[C:14](Cl)(Cl)=[O:15].C1(C)C=CC=CC=1>O>[Cl:13][C:9]1[C:5]2[C:6](=[O:8])[O:7][C:14](=[O:15])[NH:3][C:4]=2[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6371PhosgeneHCID 14797Potassium HydroxideHCID 750712-Amino-6-chlorobenzoic acid

Product 1

HCID 6390585-chloro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dioneYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of potassium hydroxide (1.68 g, 30 mmol) and 2-amino-6-chlorobenzoic acid (3.43 g, 20 mmol) in water (25 mL) at 0° C. was treated dropwise with 20% phosgene in toluene (16.8 mL, 32 mmol) resulting in a precipitate. The mixture was stirred for 1 hour and the solid was collected by filtration, washed with water and dried to give the title compound (3.6 g, 91%). 1H NMR (300 MHz, DMSO-d6) δ 7.11 (d, J=7.35 Hz, 1H), 7.31 (d, J=6.99 Hz, 1H), 7.66 (t, J=8.09 Hz, 1H), 11.83 (s, 1H).

Workup

  1. customresulting in a precipitate
  2. filtrationthe solid was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-79abdef70f2a441884f1cc982f46da51
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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