Water → (2-Chloro-5-(boc-amino)phenyl)acetonitrile

HRID 1760027Notes

Reaction equation

HRID 1760027 reaction equation
S(O[CH2:6][C:7]1[CH:12]=[C:11]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:10]=[CH:9][C:8]=1[Cl:21])(=O)(=O)C.[C-:22]#[N:23].[Na+].O>CS(C)=O>[Cl:21][C:8]1[CH:9]=[CH:10][C:11]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:12][C:7]=1[CH2:6][C:22]#[N:23]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 226001112-Chloro-5-(boc-amino)benzyl mesylate

Product 1

HCID 22600105(2-Chloro-5-(boc-amino)phenyl)acetonitrileYield 65%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of 2-chloro-5-(Boc-amino)benzyl mesylate (from step (ii) above) in DMSO was added NaCN (2.9 g; 60 mmol), and the solution was stirred at room temperature overnight. The mixture was poured into water (300 mL) and the water suspension was extracted with ether (4×50 mL). The combined organic layers were washed with water, dried (Na2SO4), and concentrated. After flash chromatography (Si-gel; heptane:EtOAc (8:2)), 5.2 g (65%) of the sub-title compound was obtained.

Workup

  1. extractionthe water suspension was extracted with ether (4×50 mL)
  2. washThe combined organic layers were washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ffb44a46310f4633bd0c5101b5e143ad
Source dataset
uspto-grants-2005_01
Patent number
US06838478B2

Reaction notes

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