Hydrochloric Acid → Methyl 4-(N-(benzofuran-5-ylmethyl)sulfamoyl)benzoate

HRID 73057

Reaktionsgleichung

Reaktionsgleichung von HRID 73057
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH2:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1.Cl[S:13]([C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1)(=[O:15])=[O:14].Cl>C(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:11][S:13]([C:16]3[CH:17]=[CH:18][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:24][CH:25]=3)(=[O:15])=[O:14])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 27951821-Benzofuran-5-ylmethylamineHCID 4738388Methyl 4-(Chlorosulfonyl)benzoate

Produkt 1

HCID 66837840Methyl 4-(N-(benzofuran-5-ylmethyl)sulfamoyl)benzoateAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of benzofuran-5-ylmethanamine (6.5 g, 28 mmol) in DCM (100 mL) was added methyl 4-(chlorosulfonyl)benzoate (4.1 g, 28 mmol) in portion wise at 0° C., and the mixture was stirred at room temperature for 3 hrs. The mixture was added 2 M aqueous HCl (80 mL) to give a white suspension. A half volume of DCM was removed by nitrogen flow, and the precipitates were collected by filtration, washed with water, and the solid was dried in vacuo at 50° C. to give 5.3 g (55% yield) of the titled compound as a off-white solid. The filtrate formed a suspension, which was collected by filtration, washed with water, and the solid was dried in vacuo at 50° C. to give 3.4 g (35% yield) of the titled compound as a pale brown white solid.

Aufarbeitung

  1. customto give a white suspension
  2. customA half volume of DCM was removed by nitrogen flow
  3. filtrationthe precipitates were collected by filtration
  4. washwashed with water
  5. customthe solid was dried in vacuo at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-d6962fdbf85542c599111db05d8ec0f7
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829026B2

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