Water → 2-(3,4-Dimethoxy-phenyl)-N-[2-(3,4-dimethoxy-phenylsulfanyl)-ethyl]-acetamide

HRID 458798Notes

Reaction equation

HRID 458798 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11][CH2:12][CH2:13][NH2:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH2:25][C:26](Cl)=[O:27])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24].O.CCOC(C)=O>C1COCC1>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH2:25][C:26]([NH:14][CH2:13][CH2:12][S:11][C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)=[O:27])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 3604458(3,4-Dimethoxyphenyl)acetyl chlorideHCID 137594312-(3,4-Dimethoxy-phenylsulfanyl)-ethylamine

Product 1

HCID 184425752-(3,4-Dimethoxy-phenyl)-N-[2-(3,4-dimethoxy-phenylsulfanyl)-ethyl]-acetamideYield 97.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (0° C.) solution of 2-(3,4-dimethoxy-phenylsulfanyl)-ethylamine (3.97 g, 18.6 mmol) in anhydrous THF (49 ml), were added TEA (3.11 ml, 18.6 mmol) and portionwise 3,4-dimethoxyphenylacetylchloride (4.0 g, 18.6 mmol). The resulting mixture was stirred at RT for 20 h under nitrogen. The mixture was combined with H2O and extracted three times with CH2Cl2. The combined organic phases were dried over anhydrous MgSO4, filtered and concentrated to give a crude solid. Flash chromatography (AcOEt) gave the title product (7.08 g, 97%).

Workup

  1. extractionextracted three times with CH2Cl2
  2. dry with materialThe combined organic phases were dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude solid

Sources & evidence

ORD record
ord-d912c89fa56e4edcb5506a9cb468c3ac
Source dataset
uspto-grants-2007_03
Patent number
US07192950B2

Reaction notes

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