Phosphorus oxychloride → 14446-29-8

HRID 2414243Notes

Reaction equation

HRID 2414243 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH2:14][CH2:15][NH:16][CH:17]=O)[CH:11]=[CH:12][CH:13]=1>CCCCCC>[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:11](=[CH:12][CH:13]=1)[CH:17]=[N:16][CH2:15][CH2:14]2

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 13562936N-[2-(3-Methoxyphenyl)ethyl]formamide

Product 1

HCID 1001219614446-29-8Yield 67.5%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Phosphorus oxychloride (80 mL, 0.85 mol) was added dropwise to N-[2-(3-methoxy-phenyl)-ethyl]-formamide (41.1 g, 0.24 mol) and refluxed for 1 hour. The reaction mixture was cooled to room temperature, and hexane (3×500 mL) was added and decanted off three times. To the dark oily solution was added slowly water (200 mL) while stirring. The mixture was basified with NaOH to pH>13, extracted with ethyl acetate, dried (Na2SO4) and concentrated to afford the desired product (26.1 g, 67%). MS: 162.1 (M+1+).

Workup

  1. temperaturerefluxed for 1 hour
  2. customdecanted off three times
  3. additionTo the dark oily solution was added slowly water (200 mL)
  4. extractionextracted with ethyl acetate
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3a48046fd77343c6842123f3793bf078
Source dataset
uspto-grants-2004_11
Patent number
US06812228B2

Reaction notes

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