2-Amino-6-chlorobenzoic acid → 5-chloro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

HRID 3101

Reaction equation

HRID 3101 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([OH:6])=[O:5].Cl[C:13]([O:16]C(=O)OC(Cl)(Cl)Cl)(Cl)Cl>O1CCCC1>[Cl:11][C:7]1[C:3]2[C:4](=[O:6])[O:5][C:13](=[O:16])[NH:1][C:2]=2[CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 750712-Amino-6-chlorobenzoic acidHCID 94429Triphosgene

Product 1

HCID 6390585-chloro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dioneYield 250.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred warm (50° C.) solution of 2-amino-6-chlorobenzoic acid (2.00 g, 11.7 mM) in tetrahydrofuran (20 mL) was added bis(trichloromethyl)carbonate (1.20 g, 4.10 mM). A vigorous gas evolution ensued along with the formation of a precipitate. The reaction mixture was allowed to cool to room temperature and the precipitate was collected by filtration and washed with ether. Air drying gave the title compound as a tan solid (2.0 g, 87%); MS(CI): 198 (M+H).

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with ether
  3. customAir drying

Sources & evidence

ORD record
ord-11cb73d43db14970822d1f7987ae94cd
Source dataset
uspto-grants-1998_03
Patent number
US05733910

Linked notes

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