Potassium Carbonate → HCID 19611382, compound

HRID 1602494Notes

Reaction equation

HRID 1602494 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([OH:40])=[C:18]([CH:39]=2)[NH:19][C:20](=[O:38])[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][C:29]3[S:30][CH:31]=[C:32]([C:34]([CH3:37])([CH3:36])[CH3:35])[N:33]=3)[CH:22]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:48][C:49]#[N:50]>CN(C)C=O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:34]([C:32]1[N:33]=[C:29]([CH2:28][O:27][C:23]2[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=2)[C:20]([NH:19][C:18]2[CH:39]=[C:14]([CH2:13][CH2:12][CH2:11][S:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)(=[O:10])=[O:9])[CH:15]=[CH:16][C:17]=2[O:40][CH2:48][C:49]#[N:50])=[O:38])[S:30][CH:31]=1)([CH3:35])([CH3:36])[CH3:37]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 19611471HCID 19611471, compound

Product 1

HCID 19611382HCID 19611382, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Procedure

5'-[3-(4-Chlorobenzenesulfonyl)propyl]-2'-hydroxy-3-[(4-tert-butyl-2-thiazolyl)methoxy]benzanilide (1.60 g, 2.67 mmol) was dissolved in dimethylformamide (16 ml), potassium carbonate (0.55 g, 4.00 mmol), a catalytically effective amount of tetrabutylammonium bromide and bromoacetonitrile (0.22 ml, 3.20 mmol) were added in that order under ice-cooling, followed by overnight stirring at room temperature. Ice-water was added to the reaction solution and the mixture was extracted twice with benzene-ethyl acetate (1:1). The resulting organic layer was washed with 5% potassium carbonate aqueous solution and brine in that order, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. By crystallizing the resulting residue from acetonitrile, 3-[(4-tert-butyl-2-thiazolyl)methoxy]-5'-[3-(4-chlorophenylsulfonyl)propyl]-2'-cyanomethoxybenzanilide was obtained as colorless crystals (1.34 g, 79%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted twice with benzene-ethyl acetate (1:1)
  3. washThe resulting organic layer was washed with 5% potassium carbonate aqueous solution and brine in that order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customBy crystallizing the resulting residue from acetonitrile

Sources & evidence

ORD record
ord-50d814e3f46e4972b756a20abf6dfb96
Source dataset
uspto-grants-1999_11
Patent number
US05981559

Reaction notes

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