Sodium Carbonate → HCID 57929898, compound

HRID 1929967Notes

Reaction equation

HRID 1929967 reaction equation
Cl.[O:2]1[CH2:6][CH2:5][NH:4][C:3]1=[NH:7].Br[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[F:19])=O.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[F:19][C:13]1[CH:14]=[C:15]([F:18])[CH:16]=[CH:17][C:12]=1[C:10]1[N:7]=[C:3]2[N:4]([CH:9]=1)[CH2:5][CH2:6][O:2]2

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27741852-Bromo-2',4'-difluoroacetophenoneHCID 178479147HCID 178479147, compound

Product 1

HCID 57929898HCID 57929898, compoundYield 26.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

The oxazolidin-2-imine hydrochloride (TCI, 5.00 g, 40.8 mmol) and 2-bromo-1-(2,4-difluorophenyl)ethanone (7.99 g, 34.0 mmol, Example #8, Step A) were dissolved in DMF (34.7 mL) then Na2CO3 (9.01 g, 85.0 mmol) was added. The mixture was stirred for about 15 min and then it was heated to about 80° C. for about 5 h. The mixture was cooled then filtered and the filtrate was concentrated under reduced pressure. The material was purified by flash chromatography on silica gel using DCM/EtOAc (gradient 1:0 to 0:1) to give the title compound (2.02 g, 26%): LC/MS (Table 1, Method g) Rt=1.94 min; MS m/z: 223.1 (M+H)+.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthen filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe material was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-cffc04ff4fe04ff3a1cc054fdb899ef8
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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