Hydrochloric Acid → N-benzyl-2-nitro-N-(4-hydroxy-3-oxobutyl)benzenesulfonamide

HRID 526733Notes

Reaction equation

[CH2:1]([N:8]([CH2:21][CH2:22][CH:23]([OH:29])[CH:24](OC)[O:25]C)[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19])(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(O)CC>[CH2:1]([N:8]([CH2:21][CH2:22][C:23](=[O:29])[CH2:24][OH:25])[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19])(=[O:10])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of N-benzyl-N-(3-hydroxy-4,4-dimethoxybutyl)-2-nitrobenzenesulfonamide (0.212 g, 0.5 mmol) in 1-Propanol (1.5 ml) was added 37% hydrochloric acid (0.104 ml, 1.250 mmol) and the mixture was stirred at 90° C. in a weaton vial. Cooled, evaporated to dryness under vacuum, applied on a column in petroleum ether-ethyl acetate mixture 1:1, eluted with the same system. Fractions collected to give N-benzyl-N-(4-hydroxy-3-oxobutyl)-2-nitrobenzenesulfonamide (0.085 g, 0.225 mmol, 44.9% yield), yellowish oil.

Workup

temperatureCooled
customevaporated to dryness under vacuum
washeluted with the same system
customFractions collected

Sources & evidence

ORD record: ord-c18f3fa059ef496bacfb1a4cf85cf768
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346751B2

Reaction notes

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