Dimethylamine → HCID 57809335, compound

HRID 2105845Notes

Reaction equation

HRID 2105845 reaction equation
[CH3:1][N:2]([CH3:21])[S:3]([C:6]1[C:7](F)=[CH:8][C:9]([O:17][CH2:18][CH3:19])=[C:10]([CH:16]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:5])=[O:4].[CH3:22][NH:23][CH3:24]>CN(C)C=O.O>[CH3:22][N:23]([CH3:24])[C:7]1[C:6]([S:3](=[O:5])(=[O:4])[N:2]([CH3:21])[CH3:1])=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:9]([O:17][CH2:18][CH3:19])[CH:8]=1

Participants

5

Reactant 2

HCID 674DimethylamineHCID 68872568HCID 68872568, compound

Product 1

HCID 57809335HCID 57809335, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 5-dimethylsulfamoyl-2-ethoxy-4-fluoro-benzoate (1.02 g, 3.20 mmol) was taken up in 5 mL of anhydrous dimethylformamide. Dimethylamine (8.0 mL, 15.9 mmol) was added and the reaction mixture was heated at 50° C. for 16 h. The reaction was allowed to cool to room temperature and diluted with water. The product was extracted three times with methylene chloride. The combined organics extracts were washed with brine, dried over magnesium sulfate and concentrated to give ethyl 4-dimethylamino-5-dimethylsulfamoyl-2-ethoxy-benzoate as a tan solid (1.05 g, 95%). LC-MS: 345.3 [(M+H)+].

Workup

  1. temperatureto cool to room temperature
  2. extractionThe product was extracted three times with methylene chloride
  3. washThe combined organics extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-39ecdde5463441cbbcf8c86d0a51ea9a
Source dataset
uspto-grants-2009_08
Patent number
US07579368B2

Reaction notes

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