1-Chloro-4-(chloromethyl)benzene → 4-Chlorobenzyl N-methyl-N-phenylglycinate

HRID 2184088

Reaction equation

HRID 2184088 reaction equation
[CH3:1][N:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5].C([O-])([O-])=O.[Cs+].[Cs+].[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=1>CN(C=O)C.CCOC(C)=O>[CH3:1][N:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][C:4]([O:6][CH2:24][C:23]1[CH:26]=[CH:27][C:20]([Cl:19])=[CH:21][CH:22]=1)=[O:5]

Participants

6

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 10796Cesium carbonateHCID 420843N-Methyl-N-phenyl-glycine

Product 1

HCID 224756194-Chlorobenzyl N-methyl-N-phenylglycinateYield 68%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product from step 2 (220 mg, 1.3 mmol) was dissolved in DMF (7 mL) and Cs2CO3 (652 mg, 2.0 mmol) added, followed by 4-chlorobenzyl chloride (214 mg, 1.3 mmol). Allow reaction mixture to stir at ambient temperature over 18 hours. The reaction mixture was diluted with EtOAc and washed several times with brine. The organic layer was dried (Na2SO4), filtered and concentrated to afford the title compound as a yellow oil (68%). MS (ES+) m/z 290 (MH+).

Workup

  1. customAllow reaction mixture
  2. washwashed several times with brine
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-438b7ff164b94e54ab70879eeafb9775
Source dataset
uspto-grants-2005_05
Patent number
US06900244B2

Linked notes

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