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

HRID 1725985Notes

Reaction equation

HRID 1725985 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].[OH-].[Na+].[C:15](Cl)(Cl)=[O:16]>O>[CH3:12][O:11][C:7]1[C:3]2[C:4](=[O:6])[O:5][C:15](=[O:16])[NH:1][C:2]=2[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 14798Sodium HydroxideHCID 27353572-Amino-6-methoxybenzoic Acid

Product 1

HCID 107502955-Methoxy-2H-3,1-benzoxazine-2,4(1H)-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-amino-6-methoxybenzoic acid (10 g, 60 mmol), water (330 mL), and sodium hydroxide (7.2 g, 176 mmol) was treated with phosgene (20% solution in toluene, 82 mL, 164 mmol) over 1 hour and filtered. The filter cake was dried to provide the desired product. MS (ESI(+)) m/e 194 (M+H)+, 211 (M+NH4)+, 216 (M+Na)+; (ESI(−)) m/e 192 (M−H)+; 1H NMR (300 MHz, DMSO-d6) δ 11.57 (s, 1H), 7.64 (t, 1H), 6.84 (d, 1H), 6.68 (d, 1H), 3.88 (s, 3H).

Workup

  1. filtrationfiltered
  2. customThe filter cake was dried

Sources & evidence

ORD record
ord-01c351cb2a4d45619bbd24cc302e345e
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

Loading…