4-Toluenesulfonyl chloride → N-(2,2-Dimethoxy-ethyl)4-methyl-N-(5-methyl-thiophen-2-ylmethyl)-benzenesulfonamide

HRID 254436Notes

Reaction equation

[CH3:1][O:2][CH:3]([O:13][CH3:14])[CH2:4][NH:5][CH2:6][C:7]1[S:8][C:9]([CH3:12])=[CH:10][CH:11]=1.C(N(CC)CC)C.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>CCOC(C)=O>[CH3:1][O:2][CH:3]([O:13][CH3:14])[CH2:4][N:5]([CH2:6][C:7]1[S:8][C:9]([CH3:12])=[CH:10][CH:11]=1)[S:28]([C:25]1[CH:26]=[CH:27][C:22]([CH3:32])=[CH:23][CH:24]=1)(=[O:30])=[O:29]

Participants

Conditions

Temperature: 0 °C

Procedure

Crude (2,2-dimethyloxy-ethyl)-(5-methyl-thiophen-2-ylmethyl)-amine (1) (43.41 g ˜75% pure, 0.15 mol) was dissolved in EtOAc (150 mL) resulting in a yellow solution. Triethylamine (22 mL, 0.16 mol) was added. The mixture was cooled to 0° C. in ice bath. p-Toluenesulfonyl chloride (29.68 g, 0.16 mol) was added in small portions keeping the temperature below 15° C. After addition was complete the mixture was left in ice bath and allowed to slowly warm to room temperature and stirred for 20 hrs. The milky-yellow mixture was diluted with EtOAc (300 mL) and washed with water (2×400 mL), 1 M HCl (2×400 mL), water (1×400 mL), sat NaHCO3 (1×400 mL), and brine (1×400 mL), dried (MgSO4) and condensed to provide the title compound as a reddish-yellow liquid, 50.56 g. Product was not purified.

Workup

customresulting in a yellow solution
customthe temperature below 15° C
additionAfter addition
waitwas left in ice bath
temperatureto slowly warm to room temperature
washwashed with water (2×400 mL), 1 M HCl (2×400 mL), water (1×400 mL)
customdried
custom(MgSO4) and condensed

Sources & evidence

ORD record: ord-9ee59b2efec0401d99b822c76a4adfbf
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07875627B2

Reaction notes

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