Triphosgene → HCID 63109414, compound

HRID 1041706Notes

Reaction equation

HRID 1041706 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 H2O. 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 H2O
  4. filtrationThe peach ppt was filtered
  5. concentrationwas concentrated under reduced pressure
  6. customIt was then azeotroped in toluene

Sources & evidence

ORD record
ord-ad44d9fa2314443c9267ae138b8bd28a
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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