Triphosgene → 5,6-Dimethoxyisatoic anhydride

HRID 525956Notes

Reaction equation

HRID 525956 reaction equation
[C:1](=O)(OC(Cl)(Cl)Cl)[O:2]C(Cl)(Cl)Cl.Cl.[NH2:14][C:15]1[C:20]([C:21]([OH:23])=[O:22])=[C:19]([O:24][CH3:25])[C:18]([O:26][CH3:27])=[CH:17][CH:16]=1>O>[CH3:25][O:24][C:19]1[C:20]2[C:21](=[O:23])[O:22][C:1](=[O:2])[NH:14][C:15]=2[CH:16]=[CH:17][C:18]=1[O:26][CH3:27]

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 1317355906-Amino-2,3-dimethoxybenzoic acid hydrochloride

Product 1

HCID 127623805,6-Dimethoxyisatoic anhydrideYield 125%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Bis(trichloromethyl) carbonate (24.89 g, 84 mmol) was added into a solution of 6-amino-2,3-dimethoxybenzoic acid, Hydrochloride (28 g, 120 mmol) in Water (1.1 L). The mixture was stirred at r.t. over the weekend. The reaction mixture was filtered, the solid was collected and dried to afford 5,6-dimethoxy-1H-benzo[d][1,3]oxazine-2,4-dione (24 g, 105 mmol, 88% yield) as a light yellow solid. LCMS: (M+H)+: 223.9.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solid was collected
  3. customdried

Sources & evidence

ORD record
ord-44a2f8d6a6894dd7b82921f6a093038a
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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