Dimethylamine → HCID 57809360, compound

HRID 2105843Notes

Reaction equation

HRID 2105843 reaction equation
Cl[S:2]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([O:15][CH2:16][CH3:17])[CH:6]=1)(=[O:4])=[O:3].[CH3:18][NH:19][CH3:20]>C(Cl)Cl>[CH3:18][N:19]([CH3:20])[S:2]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([O:15][CH2:16][CH3:17])[CH:6]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 86607796HCID 86607796, compound

Product 1

HCID 57809360HCID 57809360, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 4-chlorosulfonyl-2-ethoxy-benzoate (1.3 g, 4.55 mmol) was taken up in anhydrous methylene chloride (30 mL) and cooled to 0° C. Dimethylamine (9.1 mL, 18.2 mmol) was added. The reaction mixture was allowed to slowly warm to room temperature and stirred at room temperature for 16 h. The reaction mixture was washed with water, dried over magnesium sulfate and concentrated. Purification of the crude residue by flash column chromatography (silica gel, eluting with 20-50% ethyl acetate in hexanes) gave methyl 4-dimethylsulfamoyl-2-ethoxy-benzoate as a yellow solid (0.528 g, 41%). LC-MS: 288.1 [(M+H)+].

Workup

  1. temperatureto slowly warm to room temperature
  2. washThe reaction mixture was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customPurification of the crude residue
  6. washby flash column chromatography (silica gel, eluting with 20-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-f0571a106e0c4bedb5052c83a9f4652d
Source dataset
uspto-grants-2009_08
Patent number
US07579368B2

Reaction notes

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