Triphosgene → 8-Methoxy-1H-benzo[d][1,3]oxazine-2,4-dione

HRID 617127Notes

Reaction equation

HRID 617127 reaction equation
[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[C:14](Cl)([O:16]C(=O)OC(Cl)(Cl)Cl)Cl>O1CCCC1>[CH3:12][O:11][C:10]1[C:2]2[NH:1][C:14]([O:5][C:4](=[O:6])[C:3]=2[CH:7]=[CH:8][CH:9]=1)=[O:16]

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 2557202-Amino-3-methoxybenzoic acid

Product 1

HCID 105596798-Methoxy-1H-benzo[d][1,3]oxazine-2,4-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a chilled (0-5° C.) solution of 30.0 g (0.180 mol) of 2-amino-3-methoxybenzoic acid (Aldrich Chemicals) in 500 mL of tetrahydrofuran was added 17.8 g (0.0600 mol) of triphosgene. A precipitate formed upon addition. The ice bath was removed after 15 minutes, and the reaction mixture was stirred for 1 hour at room temperature. The reaction mixture was poured into 1000 mL of water and stirred for thirty minutes. The product (mp 267-268° C.) was filtered and amounted to 32.9 g.

Workup

  1. customA precipitate formed upon addition
  2. customThe ice bath was removed after 15 minutes
  3. additionThe reaction mixture was poured into 1000 mL of water
  4. stirringstirred for thirty minutes
  5. filtrationThe product (mp 267-268° C.) was filtered

Sources & evidence

ORD record
ord-61941d03209842d88305795814a28779
Source dataset
uspto-grants-1999_09
Patent number
US05948775

Reaction notes

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