Water → HCID 18630077, compound

HRID 1458132Notes

Reaction equation

HRID 1458132 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11]C(N)=[CH:9][C:3]=1[C:4]([NH:6][CH2:7][CH3:8])=[O:5].C(=O)([O-])[O-].[K+].[K+].CI.O.[CH3:23][N:24]([CH:26]=O)[CH3:25]>>[CH2:7]([NH:6][C:4](=[O:5])[C:3]1[CH:9]=[C:26]([N:24]([CH3:23])[CH3:25])[CH:11]=[CH:12][C:2]=1[Cl:1])[CH3:8]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 167727345-Amino-2-chloro-N-ethylbenzamide

Product 1

HCID 18630077HCID 18630077, compoundYield 29%

Procedure

A mixture of the above amine (3 g, 0.015 mol), potassium carbonate (3.8 g, 0.028 mol) and MeI (1.4 mL, 0.022 mol) in DMF stirred at RT overnight. The reaction mixture was poured into water and extracted with ether. The ether layer was washed with water and brine, dried (MgSO4) and concentrated to give an oil. Purification by flash chromatography (0-50% ethyl acetate/hexanes) gave N-ethyl 2-chloro-5-(dimethylamino)benzamide as a yellow solid in 29% yield.

Workup

  1. extractionextracted with ether
  2. washThe ether layer was washed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto give an oil
  6. customPurification by flash chromatography (0-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-881a673fe4804aaa9f5ba1f598f03537
Source dataset
uspto-grants-1998_12
Patent number
US05849723

Reaction notes

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