Dimethylamine → N,N-dimethyl-5-methoxy-2-bromophenylacetamide

HRID 1270787Notes

Reaction equation

HRID 1270787 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([Br:13])=[C:7]([CH2:9][C:10](Cl)=[O:11])[CH:8]=1.[CH3:14][NH:15][CH3:16]>CCOCC>[CH3:14][N:15]([CH3:16])[C:10](=[O:11])[CH2:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=1[Br:13]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 184515295-Methoxy-2-bromophenylacetyl chloride

Product 1

HCID 18451566N,N-dimethyl-5-methoxy-2-bromophenylacetamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

5-Methoxy-2-bromophenylacetyl chloride (60 g, 0.23 mol) is dissolved in anhydrous Et2O (400 mL), stirred and cooled in an ice bath. A 2 M solution of dimethylamine (228 mL, 0.46 mol) is added dropwise and the mixture allowed to warm to room temperature and stirred for 2 hours. Additional Et2O (500 mL) is added. The organic solution is washed with 1 N HCl (2×500 mL), saturated NaHCO3 (500 mL) and brine (500 mL). The organic layer is dried (Na2SO4) and concentrated by rotary evaporator. The residue is purified using flash chromatography (hexanes/EtOAc, from 7:3 to 1:9). Trituration of the crude product with Et2O/hexanes gives N,N-dimethyl-5-methoxy-2-bromophenylacetamide as a white crystalline solid (m.p. 88–90° C.).

Workup

  1. temperaturecooled in an ice bath
  2. stirringstirred for 2 hours
  3. washThe organic solution is washed with 1 N HCl (2×500 mL), saturated NaHCO3 (500 mL) and brine (500 mL)
  4. dry with materialThe organic layer is dried (Na2SO4)
  5. concentrationconcentrated by rotary evaporator
  6. customThe residue is purified

Sources & evidence

ORD record
ord-004c3462ebdf41948f00335f39e12ac2
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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