Sodium Cyanate → HCID 57386575, compound

HRID 1800537Notes

Reaction equation

HRID 1800537 reaction equation
Br[CH2:2][C:3]1[C:4]([Cl:13])=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].[O-][C:15]#[N:16].[Na+]>CN(C)C=O.C(OCC)(=O)C.CCCCCC>[Cl:13][C:4]1[C:3]([CH2:2][C:15]#[N:16])=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 2

HCID 517096Sodium CyanateHCID 57386060Benzoic acid, 3-(bromomethyl)-2-chloro-, methyl ester

Product 1

HCID 57386575HCID 57386575, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 3-(bromomethyl)-2-chlorobenzoate (748 mg, 2.84 mmol) in N,N-dimethylformamide (7 mL) was added sodium cyanate (412 mg, 8.41 mmol), and the mixture was stirred at 80° C. for 1 hr under nitrogen stream. The reaction mixture was diluted with a mixed solvent of ethyl acetate and hexane (1:1). The solution was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/98→20/80), and recrystallized from ethyl acetate and hexane to give the title compound (470 mg, 79%) as white crystals.

Workup

  1. washThe solution was washed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltrated
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/98→20/80)
  6. customrecrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-bb790a911b5d44918bd68644aa463dbf
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

Loading…