Potassium Hydroxide → HCID 20032358, compound

HRID 231451Notes

Reaction equation

HRID 231451 reaction equation
[CH3:1][O:2][NH:3][C:4](=[O:6])[CH3:5].[OH-].[K+].[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Br)=[C:12]([Cl:18])[CH:11]=1>O1CCCC1.C(OCC)C.C1OCCOCCOCCOCCOCCOC1>[Cl:18][C:12]1[CH:11]=[C:10]([F:9])[CH:17]=[CH:16][C:13]=1[CH2:14][N:3]([O:2][CH3:1])[C:4](=[O:6])[CH3:5]

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 138591Acetamide, N-methoxy-HCID 27250621-(Bromomethyl)-2-chloro-4-fluorobenzene

Product 1

HCID 20032358HCID 20032358, compoundYield 33.5%

Reagents, catalysts & solvents 3

HCID 2855718-Crown-6CatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of 1.95 g (0.0219 mole) of N-methoxyacetamide, 1.23 g 0.022 mole) of powdered potassium hydroxide, and a small amount (~0.05 g) of 18-crown-6 in 10 ml of tetrahydrofuran was added a solution of 5.05 g (0.0226 mole) of 4-fluoro-2-chlorobenzyl bromide in 15 ml of tetrahydrofuran. This mixture was heated at reflux for approximately 17 hours and then was allowed to cool to room temperature. The mixture was diluted with 125 ml of diethyl ether and was washed with an aqueous, saturated sodium chloride solution. The organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure leaving a yellow oil. This oil was purified by column chromatography on silica gel, eluting with ethyl acetate:n-heptane (25:75) followed by ethyl acetate:n-heptane (50:50) , to yield 1.7 g of N-(2-chloro-4-fluoro-benzyl)-N-methoxyacetamide as an oil.

Workup

  1. temperatureThis mixture was heated
  2. temperatureat reflux for approximately 17 hours
  3. washwas washed with an aqueous, saturated sodium chloride solution
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure
  7. customleaving a yellow oil
  8. customThis oil was purified by column chromatography on silica gel
  9. washeluting with ethyl acetate:n-heptane (25:75)

Sources & evidence

ORD record
ord-0762b866d1654bfe961474f9b99ac86b
Source dataset
uspto-grants-1989_07
Patent number
US04846882

Reaction notes

Loading…