p-Fluorophenethylamine → 4-[2-(4-Fluoro-phenyl)-ethylcarbamoyl]-benzenesulfonyl chloride

HRID 643998

Reaction equation

[Cl:1][S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[F:14][C:15]1[CH:23]=[CH:22][C:18]([CH2:19][CH2:20][NH2:21])=[CH:17][CH:16]=1>C(Cl)Cl>[F:14][C:15]1[CH:23]=[CH:22][C:18]([CH2:19][CH2:20][NH:21][C:9]([C:8]2[CH:12]=[CH:13][C:5]([S:2]([Cl:1])(=[O:4])=[O:3])=[CH:6][CH:7]=2)=[O:10])=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

TEA (474 μL, 3.4 mmol), is added dropwise to a suspension of the title A compound, 4-chlorosulfonyl-benzoyl chloride in DCM (10 mL) at −78° C. To this mixture is added p-fluorophenethylamine over 5 min. After another 10 min at −78° C., the solution is allowed to warm to 0° C. and stirring is continued at this temperature for 1 h. The reaction is quenched by adding it to ice-water (30 mL), and the mixture is extracted with DCM (3×10 mL). The combined organic phases are dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum to obtain the crude product which is chromatographed on silica gel using EtOAc as the eluent to give 4-[2-(4-fluoro-phenyl)-ethylcarbamoyl]-benzenesulfonyl chloride.

Workup

waitis continued at this temperature for 1 h
customThe reaction is quenched
additionby adding it to ice-water (30 mL)
extractionthe mixture is extracted with DCM (3×10 mL)
dry with materialThe combined organic phases are dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated under vacuum
customto obtain the crude product which
customis chromatographed on silica gel

Sources & evidence

ORD record: ord-dd90f2032a8d4d06b81842de02cda08b
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700637B2

Linked notes

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