Butylamine → N-butyl-2-phenoxyacetamide

HRID 651046Notes

Reaction equation

HRID 651046 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].[O:6]([CH2:13][C:14](Cl)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(Cl)Cl>[CH2:1]([NH:5][C:14](=[O:15])[CH2:13][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 69703Phenoxyacetyl chloride

Product 1

HCID 5011881N-butyl-2-phenoxyacetamideYield 104.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

A 100 mL 3-neck, round-bottom flask was charged with N-butylamine (8 mL, 80 mmol) and CH2Cl2 (20 mL) under N2 purge. The reaction was cooled to −10° C. Phenoxylacetylchloride (2.8 mL, 20 mmol) was slowly added via syringe, and the reaction was stirred at −10° C. for 5 minutes and warmed to room temperature. After 2 hours, the solvent was removed under vacuum. The reaction was diluted with water and extracted with EtOAc (3×20 mL). The combined organic layers were washed with brine (20 mL), dried (Na2SO4), filtered, and concentrated under vacuum. The pale yellow oil crystallized upon standing to provide 4.32 g of the title compound as a pale yellow crystalline solid. MS (DCI/NH3) m/z 225 (M+H)+.

Workup

  1. custompurge
  2. temperaturewarmed to room temperature
  3. waitAfter 2 hours
  4. customthe solvent was removed under vacuum
  5. additionThe reaction was diluted with water
  6. extractionextracted with EtOAc (3×20 mL)
  7. washThe combined organic layers were washed with brine (20 mL)
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum
  11. customThe pale yellow oil crystallized

Sources & evidence

ORD record
ord-173ba56b755e4dc5a657b354d911abd0
Source dataset
uspto-grants-2001_08
Patent number
US06277871B1

Reaction notes

Loading…