Pyridine → HCID 18962878, compound

HRID 1707231Notes

Reaction equation

HRID 1707231 reaction equation
N1C=CC=CC=1.C(N(C(C)C)C(C)C)C.[Cl:16][CH:17]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:18](Cl)=[O:19].[CH3:27][C:28]([NH:38][CH2:39][CH:40]=[CH2:41])([C:30]1[CH:35]=[C:34]([Cl:36])[CH:33]=[C:32]([Cl:37])[CH:31]=1)[CH3:29]>ClCCl.O>[CH3:29][C:28]([N:38]([CH2:39][CH:40]=[CH2:41])[C:18](=[O:19])[CH:17]([Cl:16])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:30]1[CH:31]=[C:32]([Cl:37])[CH:33]=[C:34]([Cl:36])[CH:35]=1)[CH3:27]

Participants

7

Reactant 4

HCID 1049PyridineHCID 81531DiisopropylethylamineHCID 102902Chloro(phenyl)acetyl chlorideHCID 18962879HCID 18962879, compound

Product 1

HCID 18962878HCID 18962878, compoundYield 73.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

In 15 ml of dichloromethane containing 1.3 g of pyridine and 0.53 g of N-ethyldiisopropylamine, 2 ml of a dichloromethane solution containing 0.93 g of 2-chloro-2-phenylacetyl chloride were added dropwise to 1.0 g of N-[1-methyl-1-(3,5-dichlorophenyl)ethyl]-2-propenylamine at ice subzero temperature. Afterward, the solution was stirred at room temperature for 1 hour, and then poured into water, followed by extraction with ethyl acetate. The resultant extract was washed with a saturated aqueous sodium bicarbonate solution, and then dried over anhydrous magnesium sulfate. After concentration, column chromatography was done to obtain 1.2 g of the desired N-[1-methyl-1-(3,5dichlorophenyl)ethyl]-N-(2-propenyl)-2-chloro-2-phenylacetamide.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. extractionThe resultant extract
  3. washwas washed with a saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationAfter concentration, column chromatography

Sources & evidence

ORD record
ord-bdcf32ef95074616bd2e1dfe29924d3d
Source dataset
uspto-grants-1994_10
Patent number
US05352655

Reaction notes

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