Hydrochloric Acid → 2-(2-Amino-ethyl)-4-chloro-benzenesulfonamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:14](=[O:17])(=[O:16])[NH2:15])=[C:6]([CH2:8][CH2:9][NH:10]C(=O)C)[CH:7]=1.[OH-].[K+].Cl>>[NH2:10][CH2:9][CH2:8][C:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[S:14]([NH2:15])(=[O:17])=[O:16]Participants
4
Conditions
- Temperature
- 100 °C
Procedure
A mixture of N-[2-(5-chloro-2-sulfamoyl-phenyl)-ethyl]-acetamide (209 mg, 0.76 mmol) and potassium hydroxide aqueous solution (2 mol/L, 3 mL, 6 mmol) was stirred at 100° C. for 4 h. After cooling to room temperature, the reaction was neutralized with 2N of aqueous hydrochloric acid solution. The mixture was concentrated to dryness and the residue was diluted with solvent (3% MeOH in DCM, 200 mL) and stirred for 1 h. The mixture was filtered and the filtrate was concentrated to afford the title compound as a gray solid (150 mg, 0.64 mmol, 85% yield). MS (ESI) m/z 235.1, 237.1 [M+H]+.
Workup
- temperatureAfter cooling to room temperature
- concentrationThe mixture was concentrated to dryness
- additionthe residue was diluted with solvent (3% MeOH in DCM, 200 mL)
- stirringstirred for 1 h
- filtrationThe mixture was filtered
- concentrationthe filtrate was concentrated
Sources & evidence
- ORD record
- ord-06c907a6464e43dfb7cf20f66f967afb
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156798B2
Reaction notes
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