Water → HCID 19085381, compound

HRID 962433Notes

Reaction equation

HRID 962433 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([NH:16][C:17](=[O:26])[C:18]1[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:19]=1[F:25])[CH2:9][CH2:10]OS(C)(=O)=O.C(N(CC)CC)C.O>O1CCOCC1>[F:24][C:23]1[CH:22]=[CH:21][CH:20]=[C:19]([F:25])[C:18]=1[C:17]1[O:26][CH2:10][CH2:9][CH:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Br:1])[N:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 86752684HCID 86752684, compound

Product 1

HCID 19085381HCID 19085381, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 18.0 g of N-[1-(2-bromophenyl)-3-(methylsulfonyloxy)propyl]-2, 6-difluorobenzamide in 150ml of dioxane at room temperature, was added dropwise 4.5 g of triethylamine. The reaction mixture was refluxed for 2.5 hours. After cooling, the reaction mixture was poured into iced water and extracted with ethyl acetate. The ethyl acetate solution was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to afford 12.5 g of 2-(2,6-difluorophenyl)-4-(2-bromophenyl)-5,6-dihydro-4H-1,3-oxazine.

Workup

  1. temperatureThe reaction mixture was refluxed for 2.5 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate solution was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e436bd092d8e4d6c9883dd9b957f72f8
Source dataset
uspto-grants-1998_06
Patent number
US05760033

Reaction notes

Loading…