Triphosgene → 5-Methoxy-2H-3,1-benzoxazine-2,4(1H)-dione

HRID 3113

Reaction equation

HRID 3113 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:3]=1[C:4]([OH:6])=[O:5].Cl[C:14]([O:17]C(=O)OC(Cl)(Cl)Cl)(Cl)Cl>O1CCCC1>[CH3:12][O:11][C:7]1[C:3]2[C:4](=[O:6])[O:5][C:14](=[O:17])[NH:1][C:2]=2[CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 27353572-Amino-6-methoxybenzoic Acid

Product 1

HCID 107502955-Methoxy-2H-3,1-benzoxazine-2,4(1H)-dioneYield 283.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred warm (50° C.) solution of 2-amino-6-methoxybenzoic acid (2.70 g, 16.2 mM) in tetrahydrofuran (25 mL) under a nitrogen atmosphere was added bis(trichloromethyl)carbonate (1.60 g, 5.38 mM), whereupon a tan precipitate formed. The reaction mixture was maintained at 50° C. for 30 min, cooled, rewarmed to 50° C. for 30 min, filtered cool and dried to provide the title compound (2.95 g, 94.6%) as an off-white solid; MS(CI): 194 (M+H).

Workup

  1. customwhereupon a tan precipitate formed
  2. temperaturecooled
  3. filtrationfiltered
  4. temperaturecool
  5. customdried

Sources & evidence

ORD record
ord-566fc546dbbd4317ba914612b55bdb28
Source dataset
uspto-grants-1998_03
Patent number
US05733910

Linked notes

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