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Phenylmethanesulfonyl chloride → 2-(4-Chlorophenoxy-methyl)-2-benzylsulfonylamino-propionitrile

HRID 2221132
Notes
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Reaction equation

HRID 2221132 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]([NH2:12])([CH3:11])[C:9]#[N:10])=[CH:4][CH:3]=1.[CH2:15]([S:22](Cl)(=[O:24])=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>N1C=CC=CC=1.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]([NH:12][S:22]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:24])=[O:23])([CH3:11])[C:9]#[N:10])=[CH:13][CH:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 74740Phenylmethanesulfonyl chlorideHCID 116585482-Amino-3-(4-chlorophenoxy)-2-methylpropanenitrile

Product 1

HCID 116247712-(4-Chlorophenoxy-methyl)-2-benzylsulfonylamino-propionitrile

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

suspension of 1-(4-chloro-phenoxy)-propan-2-one (3.7 g, 20 mmol), ammonium chloride (1.6 g, 29.2 mmol) and sodium cyanide (1.15 g, 23.3 mmol) in a solution of aqueous ammonia (100 ml, 28%) is stirred vigorously at room temperature for 20 hours. The aqueous phase is extracted repeatedly with ethyl acetate. The collected organic extracts are dried and the solvent is evaporated under reduced pressure to give the 2-(4-chlorophenoxy-methyl)-2-amino-propionitrile as a solid. c) A solution of 2-(4-chlorophenoxy-methyl)-2-amino-propionitrile (0.5 g, 2.4 mmol) and benzylsulfonyl chloride (0.5 g, 2.6 mmol) in pyridine (5 ml) is heated at +80° C. with stirring in the presence of DMAP (0.02 g) 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 product is purified by flash chromatography (eluent: ethyl acetate/hexanes 1:3) to give the 2-(4-chlorophenoxy-methyl)-2-benzylsulfonylamino-propionitrile in form of a colorless solid, m.p. 120-121° C.

Workup

  1. washwashed with brine
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. customthe product is purified by flash chromatography (eluent: ethyl acetate/hexanes 1:3)

Sources & evidence

ORD record
ord-c524c7a8def844a08fe5861c4daf0625
Source dataset
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07368479B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes