Chloride → HCID 22719823, compound

HRID 1582077Notes

Reaction equation

HRID 1582077 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:16])[CH:12]=[C:13]([CH3:15])[CH3:14])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[Cl-]>C(Cl)Cl>[CH:1]([C:4]1[CH:5]=[C:6]2[C:7](=[CH:8][CH:9]=1)[NH:10][C:11](=[O:16])[CH2:12][C:13]2([CH3:14])[CH3:15])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 312ChlorideHCID 19177440HCID 19177440, compound2×

Product 1

HCID 22719823HCID 22719823, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methyl-but-2-enoic acid (4-isopropyl-phenyl)-amide (Intermediate 1, 8.12 g, 37.4 mmol) in 100 ml of anhydrous CH2Cl2 under argon at 0° C. was slowly added aluninum chloride (20 g, 150 mmol) through a powder addition fumnel. The cooling bath was removed and the mixture was stirred at ambient temperature for 3 hours. The reaction was re-cooled to 0° C. and slowly quenched with ice. The product was extracted with diethyl ether. The organic layer was washed with water, saturated NaHCO3 and brine, dried over Na2SO4, concentrated in vacuo and purified by column chromatography (silica, first using 25% ethyl acetate in hexane followed by 50% ethyl acetate in hexane) to give the title compound as a white solid.

Workup

  1. customat 0° C.
  2. additionthrough a powder addition fumnel
  3. customThe cooling bath was removed
  4. temperatureThe reaction was re-cooled to 0° C.
  5. customslowly quenched with ice
  6. extractionThe product was extracted with diethyl ether
  7. washThe organic layer was washed with water, saturated NaHCO3 and brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. custompurified by column chromatography (silica

Sources & evidence

ORD record
ord-2fa3eb9ce2c34f4899f73cc31ce7aa48
Source dataset
uspto-grants-2004_05
Patent number
US06734193B1

Reaction notes

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