(4-Chlorophenyl)methanesulfonyl chloride → 2-(4-Chlorophenoxy-methyl)-2-(4-chlorophenyl-methylsulfonyl)-propionitrile

HRID 2221136Notes

Reaction equation

HRID 2221136 reaction equation
N[C:2]([CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)([CH3:5])[C:3]#[N:4].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][S:23](Cl)(=[O:25])=[O:24])=[CH:18][CH:17]=1.N1(C2CCCCCCC2)CCCCCCN1>O1CCCC1.C(OCC)(=O)C>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([O:7][CH2:6][C:2]([S:23]([CH2:22][C:19]2[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=2)(=[O:24])=[O:25])([CH3:5])[C:3]#[N:4])=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 227304(4-Chlorophenyl)methanesulfonyl chlorideHCID 116585482-Amino-3-(4-chlorophenoxy)-2-methylpropanenitrileHCID 66583054Diazabicyclooctane

Product 1

HCID 688017192-(4-Chlorophenoxy-methyl)-2-(4-chlorophenyl-methylsulfonyl)-propionitrile

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-amino-2-(4-chlorophenoxymethyl)-propionitrile (0.5 g, 0.24 mmol), 4-chlorophenyl-methylsulfonyl chloride (0.46 g, 2.4 mmol) and diazabicyclooctane (0.6 g, 2.4 mmol) in anhydrous tetrahydrofuran (20 ml) is stirred for about 16 hours. The reaction mixture is diluted with ethyl acetate and washed with brine. The organic phase is dried over magnesium sulfate and the raw product received as the residue is purified by flash chromato-graphy (eluent: ethyl acetate/hexanes 1:3) to give the 2-(4-chlorophenoxy-methyl)-2-(4-chlorophenyl-methylsulfonyl)-propionitrile in form of colorless crystals, m.p. 119-120° C.

Workup

  1. washwashed with brine
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. customis purified by flash chromato-graphy (eluent: ethyl acetate/hexanes 1:3)

Sources & evidence

ORD record
ord-8b0cf9c087a341c9ac98a768bbedf6a6
Source dataset
uspto-grants-2008_05
Patent number
US07368479B2

Reaction notes

Loading…