Water → HCID 20446216, compound

HRID 2418382Notes

Reaction equation

HRID 2418382 reaction equation
NC1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].CI.C(=O)([O-])[O-].[K+].[K+].O.[CH3:31][N:32]([CH3:35])[CH:33]=O>>[CH3:31][N:32]([CH3:35])[C:33]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 20446151HCID 20446151, compound

Product 1

HCID 20446216HCID 20446216, compound

Procedure

A mixture of ethyl 2-[2-amino-3-(2-chlorophenoxy)phenyl]acetate (11.8 g), methyl iodide (11.9 g) and potassium carbonate (10.7 g) in dried dimethylformamide (100 ml) was stirred at room temperature for 17 hrs. The reaction mixture was poured into water (400 ml) and extracted with diethyl ether (150 ml×2). The extract was washed with saline, dried over magnesium sulfate and evaporated in vacuo. The oily residue (12.7 g) was subjected to column chromatography on silica gel and eluted with a mixture of benzene and n-hexane (1:1) to give oily ethyl 2-[2-dimethylamino-3-(2-chlorophenoxy)phenyl]acetate (7.4 g).

Workup

  1. extractionextracted with diethyl ether (150 ml×2)
  2. washThe extract was washed with saline
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. washeluted with a mixture of benzene and n-hexane (1:1)

Sources & evidence

ORD record
ord-b2bd9422fe69499caa48acfd4cddc28c
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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