Triphosgene → 5-Fluoroisatoic anhydride

HRID 1186089Notes

Reaction equation

HRID 1186089 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[C:13](Cl)([O:15]C(=O)OC(Cl)(Cl)Cl)Cl>O1CCCC1>[F:11][C:8]1[CH:9]=[CH:10][C:2]2[NH:1][C:13](=[O:15])[O:5][C:4](=[O:6])[C:3]=2[CH:7]=1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 1014122-Amino-5-fluorobenzoic acid

Product 1

HCID 2885605-Fluoroisatoic anhydrideYield 230.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a separate preparation, 2-amino-5-fluorobenzoic acid (15 g, 97 mmol) was dissolved in tetrahydrofuran (250 mL) and triphosgene (10.04 g, 33.8 mmol) was added portion-wise. A thick white precipitate formed with a small exotherm. The slurry gradually became easier to stir and was left stirring at room temperature for 16 h. The mixture was filtered to provide a white solid which was rinsed with diethyl ether then dried at 50° C. in a vacuum over to give 6-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione (14.1 g, 78 mmol). The 6-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione may be converted to a 7-fluoro-1-(4-methoxybenzyl)-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione using the procedures described in Example 1.

Workup

  1. customA thick white precipitate formed with a small exotherm
  2. waitwas left
  3. stirringstirring at room temperature for 16 h
  4. filtrationThe mixture was filtered
  5. customto provide a white solid which
  6. washwas rinsed with diethyl ether
  7. customthen dried at 50° C. in a vacuum over

Sources & evidence

ORD record
ord-e9c5611f87df4311b056d5a271ae0f8e
Source dataset
uspto-grants-2014_03
Patent number
US08673897B2

Reaction notes

Loading…