p-Bromobenzenesulfonyl chloride → 4-Bromo-N-[4-(1-propyl-azetidin-3-yl)-phenyl]-benzenesulfonamide

HRID 1260248Notes

Reaction equation

HRID 1260248 reaction equation
[CH2:1]([N:4]1[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH2:5]1)[CH2:2][CH3:3].[Br:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>C(Cl)Cl.N1C=CC=CC=1>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:14][C:11]2[CH:10]=[CH:9][C:8]([CH:6]3[CH2:5][N:4]([CH2:1][CH2:2][CH3:3])[CH2:7]3)=[CH:13][CH:12]=2)(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 57470084HCID 57470084, compound

Product 1

HCID 670714264-Bromo-N-[4-(1-propyl-azetidin-3-yl)-phenyl]-benzenesulfonamideYield 51.2%

Reagents, catalysts & solvents 1

HCID 21875418Pyridine methylene chlorideSolvent

Procedure

Following the same procedure as described in example 55, 4-(1-propyl-azetidin-3-yl)phenylamine (1 g, 5.25 mmol) in CH2Cl2/pyridine 9:1 (50 ml) was treated with 4-bromobenzenesulfonyl chloride (1.34 g, 5.25 mmol). Purification of the crude product by flash column chromatography (CH2Cl2:methanol, 95:5) provided the title compound (1.1 g, 51%) as a colourless gum.

Workup

  1. customPurification of the crude product by flash column chromatography (CH2Cl2:methanol, 95:5)

Sources & evidence

ORD record
ord-dbad0849fb5e4c48a86355af1268b52b
Source dataset
uspto-grants-2013_06
Patent number
US08470810B2

Reaction notes

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