Triphosgene → HCID 63109414, compound

HRID 1688048Notes

Reaction equation

HRID 1688048 reaction equation
[NH2:1][C:2]1[C:10]([F:11])=[CH:9][C:8]([F:12])=[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>[F:12][C:8]1[CH:9]=[C:10]([F:11])[C:2]2[NH:1][C:14](=[O:16])[O:5][C:4](=[O:6])[C:3]=2[CH:7]=1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 146519732-Amino-3,5-difluorobenzoic acid

Product 1

HCID 63109414HCID 63109414, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Amino-3,5-difluoro-benzoic acid (2.44 g, 0.0141 mol) was dissolved in Tetrahydrofuran (100 mL). Triphosgene (4.18 g, 0.0141 mol) was dissolved in Tetrahydrofuran (10 mL) and added. The resulting solution was stirred for 4 h at rt. The reaction mixture was concentrated, and the resulting residue was sonicated in H20. The peach ppt was filtered, taken up in acetone, and was concentrated under reduced pressure. It was then azeotroped in toluene to give 6,8-Difluoro-1H-3,1-benzoxazine-2,4-dione as tan solids (2.64 g, 94%). 1H-NMR (DMSO): 12.00 (s, 1H), 7.85 (m, 1H), 7.60 (m, 1H); 19F-NMR (DMSO): −116, −125.

Workup

  1. additionadded
  2. concentrationThe reaction mixture was concentrated
  3. customthe resulting residue was sonicated in H20
  4. filtrationThe peach ppt was filtered
  5. concentrationwas concentrated under reduced pressure
  6. customIt was then azeotroped in toluene

Sources & evidence

ORD record
ord-422dacc466cc4187b9af9336079a037f
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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