Sodium Cyanate → HCID 57386575, compound

HRID 1800701Notes

Reaction equation

HRID 1800701 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

5

Reactant 2

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

Product 1

HCID 57386575HCID 57386575, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

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. The reaction mixture was diluted with a mixed solvent of ethyl acetate/hexane (1:1). The solution was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/98→20/80), and the fractions containing the object product were concentrated under reduced pressure. The obtained residue was 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. filtrationThe insoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/98→20/80)
  6. additionthe fractions containing the object product
  7. concentrationwere concentrated under reduced pressure
  8. customThe obtained residue was recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-a444a9df014f4168a7ff89fa522b8952
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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