Chloroacetic Acid → HCID 86606908, compound

HRID 2116767Notes

Reaction equation

HRID 2116767 reaction equation
[N:1]1([NH:7][C:8](=[O:18])[C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([C:16]#[N:17])[CH:10]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:28][C:29]([OH:31])=[O:30]>CC(C)=O>[N:1]1([NH:7][C:8](=[O:18])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:28][C:29]([OH:31])=[O:30])=[C:11]([C:16]#[N:17])[CH:10]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 300Chloroacetic AcidHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 86606906HCID 86606906, compound

Product 1

HCID 86606908HCID 86606908, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-Cyano-4-hydroxybenzoic acid (4-morpholinyl)amide (232 mg, 1.0 mmol), sodium iodide (150 mg, 1.0 mmol), potassium carbonate (415 mg, 3.0 mmol) and chloroacetic acid (189 mg, 2.0 mmol) are suspended in acetone (12 mL) and refluxed for 5 hours. The reaction solution is evaporated to remove the solvent under reduced pressure, partitioned by adding water and ethyl acetate, and adjusted to pH=2-3 with hydrochloric acid. The aqueous layer is separated and re-extracted with ethyl acetate (×2). The solutions are combined and washed with saturated brine. The organic layer is dried over magnesium sulfate, and evaporated to remove the solvent under reduced pressure. The precipitated crude crystals are suspended in methanol-diethyl ether, and filtered to give 3-cyano-4-carboxymethoxybenzoic acid (4-morpholinyl)amide (241 mg, 83%). Mp: 205-206° C.

Workup

  1. temperaturerefluxed for 5 hours
  2. customThe reaction solution is evaporated
  3. customto remove the solvent under reduced pressure
  4. custompartitioned
  5. additionby adding water and ethyl acetate
  6. customThe aqueous layer is separated
  7. extractionre-extracted with ethyl acetate (×2)
  8. washwashed with saturated brine
  9. dry with materialThe organic layer is dried over magnesium sulfate
  10. customevaporated
  11. customto remove the solvent under reduced pressure
  12. customThe precipitated crude crystals
  13. filtrationfiltered

Sources & evidence

ORD record
ord-0462a72c6a8b48f1b545fbebbc140bf4
Source dataset
uspto-grants-2008_10
Patent number
US07439368B2

Reaction notes

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