2-Bromo-1-(4-fluorophenyl)ethan-1-one → HCID 57433608, compound

HRID 600253Notes

Reaction equation

HRID 600253 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=[O:4].[NH2:12][C:13]1[O:14][CH:15]=[CH:16][N:17]=1>O1CCCC1.C(#N)C>[BrH:1].[F:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][N:17]2[CH:16]=[CH:15][O:14][C:13]2=[NH:12])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 5585212-Aminooxazole

Product 1

HCID 57433608HCID 57433608, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-bromo-1-(4-fluorophenyl)-ethanone (CAS# 403-29-2, I) (60 g, 0.376 mol) in anhydrous tetrahydrofuran (THF) solution (200 ml) was added over 20 minutes a solution of 2-amino-oxazole (A) (16 g, 0.19 mol) in anhydrous acetonitrile at room temperature. The mixture was stirred for 24 hours before cooling to 0° C. The precipitate was collected by filtration and washed with cold acetonitrile (3×30 mL) and dried in a vacuum oven to yield light yellow crystals of 1-(4-fluorophenyl)-2-(2-imino-1,3-oxazol-3(2H)-yl)ethanone hydrobromide (B) (42.0 g, 77%). MS (ES+) 203 (M+1).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with cold acetonitrile (3×30 mL)
  3. customdried in a vacuum oven

Sources & evidence

ORD record
ord-e35f9844b915472f93308228be447cf8
Source dataset
uspto-grants-2011_03
Patent number
US07902192B2

Reaction notes

Loading…