Acetyl chloride → HCID 22388588, compound
Reaction equation
N[C:2]1[CH:3]=[C:4]([C:8]2[CH:24]=[CH:23][C:11]([O:12][CH:13]([CH3:22])[CH2:14][NH:15][S:16]([CH:19]([CH3:21])[CH3:20])(=[O:18])=[O:17])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:25]([N:27](CC)CC)[CH3:26].C(Cl)(=[O:34])C>C(Cl)Cl>[CH3:22][CH:13]([O:12][C:11]1[CH:23]=[CH:24][C:8]([C:4]2[CH:5]=[CH:6][C:7]([NH:27][C:25](=[O:34])[CH3:26])=[CH:2][CH:3]=2)=[CH:9][CH:10]=1)[CH2:14][NH:15][S:16]([CH:19]([CH3:21])[CH3:20])(=[O:18])=[O:17]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of {2-[4-(3-Aminophenyl)phenoxy]propyl}[(methylethyl)sulfonyl]amine (125 mg, 0.3587 mmol, prepared in example 3) in methylene chloride (2.5 mL) in a 10 mL round-bottomed flask, in an ice bath, fitted with a thermometer, and under a nitrogen system was added triethylamine (0.125 mL, 0.8968 mmol). The mixture was cooled to 0° C. and acetyl chloride 0.04 mL, 0.5381 mmol) was added by syringe. The mixture was allowed to warm to room temperature, and stirred overnight, under a nitrogen system. The reaction was quenched with excess water, and the organic layer was dried with anhydrous sodium sulfate, filtered, and concentrated under reduced vacuum, yielding 265 mg viscous oil. Purification was conducted using a Chromatotron®, on a 4000 μm rotor and eluting with a 1:1 hexane:ethyl acetate solvent system, yielding the title compound (104 mg, 74%) as a slow crystallizing foam.
Workup
- temperatureto warm to room temperature
- customThe reaction was quenched with excess water
- dry with materialthe organic layer was dried with anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced vacuum
Sources & evidence
- ORD record
- ord-67760abd547143d891174b4db4ba1091
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06911476B2
Reaction notes
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