Water → HCID 18630077, compound

HRID 1068356Notes

Reaction equation

HRID 1068356 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-1e05aba9290c4f43a7bf6b32f39f3e1a
Source dataset
uspto-grants-2001_06
Patent number
US06248894B1

Reaction notes

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