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

HRID 73057

Reaction equation

HRID 73057 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-d6962fdbf85542c599111db05d8ec0f7
Source dataset
uspto-grants-2014_09
Patent number
US08829026B2

Linked notes

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