Dimethylamine → HCID 68872568, compound

HRID 2105844Notes

Reaction equation

HRID 2105844 reaction equation
Cl[S:2]([C:5]1[C:6]([F:19])=[CH:7][C:8]([O:16][CH2:17][CH3:18])=[C:9]([CH:15]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:4])=[O:3].[CH3:20][NH:21][CH3:22]>C(Cl)Cl>[CH3:20][N:21]([CH3:22])[S:2]([C:5]1[C:6]([F:19])=[CH:7][C:8]([O:16][CH2:17][CH3:18])=[C:9]([CH:15]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 86607797HCID 86607797, compound

Product 1

HCID 68872568HCID 68872568, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 5-chlorosulfonyl-2-ethoxy-4-fluorobenzoate (1.5 g, 4.84 mmol; prepared as described in example 2) was taken up in 36 mL of anhydrous methylene chloride and cooled to 0° C. Dimethylamine (7.3 mL, 14.5 mmol) was added and the reaction mixture was stirred at 0° C. for 2 h and concentrated in vacuo. Purification of the crude residue by flash column chromatography (silica gel, eluting with 20-40% ethyl acetate in hexanes) gave ethyl 5-dimethylsulfamoyl-2-ethoxy-4-fluoro-benzoate as a white solid (1.02 g, 68%). LC-MS: 320.2 [(M+H)+].

Workup

  1. concentrationconcentrated in vacuo
  2. customPurification of the crude residue
  3. washby flash column chromatography (silica gel, eluting with 20-40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-324c3ad7319047438f20c5f22f84a524
Source dataset
uspto-grants-2009_08
Patent number
US07579368B2

Reaction notes

Loading…