Water → HCID 19085381, compound

HRID 962431Notes

Reaction equation

HRID 962431 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([NH:12][C:13](=[O:22])[C:14]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=1[F:21])[CH2:9][CH2:10]Cl.[H-].[Na+].O>CN(C)C=O>[F:21][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([F:20])[C:14]=1[C:13]1[O:22][CH2:10][CH2:9][CH:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Br:1])[N:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 19085382HCID 19085382, compound

Product 1

HCID 19085381HCID 19085381, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 10.0 g of N-[1-(2-bromophenyl)-3-chloropropyl]-2,6-difluorobenzamide in 60 ml of N,N-dimethylformamide at a temperature of from 5° C. to 10° C., was added portionwise 1.1 g of 60% dispersion in mineral oil of sodium hydride. The reaction mixture was stirred at room temperature for 2 hours. 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 7.4 g of 2-(2,6-difluorophenyl)-4-(2-bromophenyl)-5,6-dihydro-4H-1,3-oxazine. ND23.0 1.5750

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate solution was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-85ae056632fd4e5dbf8f15f523b1bee9
Source dataset
uspto-grants-1998_06
Patent number
US05760033

Reaction notes

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