Pyridine → N-(2,2-dimethoxyethyl)-4-methyl-N-(thiophen-2-ylmethyl)benzenesulfonamide

HRID 507674Notes

Reaction equation

[CH3:1][O:2][CH:3]([O:12][CH3:13])[CH2:4][NH:5][CH2:6][C:7]1[S:8][CH:9]=[CH:10][CH:11]=1.N1C=CC=CC=1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>ClCCl>[CH3:1][O:2][CH:3]([O:12][CH3:13])[CH2:4][N:5]([CH2:6][C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[S:26]([C:23]1[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=1)(=[O:28])=[O:27]

Participants

Conditions

Temperature: 0 °C

Procedure

2,2-Dimethoxy-N-(thiophen-2-ylmethyl)ethanamine (5 g, 24 mmol) was dissolved in anhydrous dichloromethane and pyridine (5.82 mL, 72 mmol) was added to the reaction. The mixture was cooled down to 0° C. and was treated with para-toluenesulfonyl chloride (5.6 g, 29 mmol) added portionwise. The reaction was allowed to stir at 0° C. for 4 h and was then washed 3 times with 1 N HCl, water and a saturated solution of sodium bicarbonate. The organic layer was dried with sodium sulfate. Purification by flash chromatography using a gradient of 5-30% ethyl acetate in hexanes yielded a white crystalline solid (7.4 g) MS (M+H)+ 356.

Workup

additionadded portionwise
washwas then washed 3 times with 1 N HCl, water
dry with materialThe organic layer was dried with sodium sulfate
customPurification by flash chromatography

Sources & evidence

ORD record: ord-43b115ad702b427da888fe5f8f04395f
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786132B2

Reaction notes

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