Triethylamine → N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}pyrid-3-ylsulfonamide

HRID 413022Notes

Reaction equation

C(N(CC)CC)C.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[N:16]2[CH2:19][CH:18]([NH2:20])[CH2:17]2)=[CH:11][CH:10]=1.[N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([S:34](Cl)(=[O:36])=[O:35])[CH:29]=1>ClCCl>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[N:16]2[CH2:17][CH:18]([NH:20][S:34]([C:30]3[CH:29]=[N:28][CH:33]=[CH:32][CH:31]=3)(=[O:36])=[O:35])[CH2:19]2)=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

0.79 cm3 of triethylamine is added, at room temperature under an argon atmosphere, to a solution of 0.7 g of 1-[bis(4-chlorophenyl)methyl]azetidin-3-ylamine in 25 cm3 of dichloromethane. The mixture is cooled to around 0° C. before adding thereto a solution of 1.2 g of pyrid-3-ylsulfonyl chloride in 25 cm3 of dichloromethane, and then it is stirred at room temperature for 16 hours. The reaction mixture is diluted with 50 cm3 of dichloromethane and is then washed with twice 25 cm3 of distilled water. The organic phase is dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is purified by flash chromatography on silica gel [eluant: dichloromethane/methanol (97.5/2.5 by volume)]. 0.7 g of N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}pyrid-3-ylsulfonamide is obtained in the form of a cream-colored foam which solidifies in the presence of isopropanol into a cream-colored powder melting at 164° C.

Workup

additionbefore adding
washis then washed with twice 25 cm3 of distilled water
dry with materialThe organic phase is dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
customThe residue obtained
customis purified by flash chromatography on silica gel [eluant: dichloromethane/methanol (97.5/2.5 by volume)]

Sources & evidence

ORD record: ord-fd0877337ff3403f85c58207abc4d173
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06566356B2

Reaction notes

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