Water → N-benzyl-N-(4-bromo-3-oxobutyl)-2-nitrobenzenesulfonamide

HRID 526723Notes

Reaction equation

[CH2:1]([N:8]([CH2:21][CH2:22][C:23](=[O:25])[CH3:24])[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.[Br:26]Br.O>CO>[CH2:1]([N:8]([CH2:21][CH2:22][C:23](=[O:25])[CH2:24][Br:26])[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: 30 °C

Procedure

To a solution of N-benzyl-2-nitro-N-(3-oxobutyl)benzenesulfonamide (compound F, 30 g, 83 mmol) in methanol (300 ml) was added bromine (4.69 ml, 91 mmol) in one portion at 20-25° C. Stirred for 20 hours (no bromine colour), water (20 ml) added, heated to reflux for 30 min, diluted with MeOH (100 ml). The solution was cooled to 30° C. with stirring, seeded with compound G, stirred at 25-30° C. for 5 min (crystallisation occurred), cooled to 15° C., aged for 1 hour. Crystals collected, washed with 2×15 ml of MeOH (20-25° C.), dried on air to give N-benzyl-N-(4-bromo-3-oxobutyl)-2-nitrobenzenesulfonamide (19.4 g, 44.0 mmol, 53.1% yield).

Workup

additionadded
temperatureheated
temperatureto reflux for 30 min
stirringstirred at 25-30° C. for 5 min
custom(crystallisation occurred)
temperaturecooled to 15° C.
customCrystals collected
washwashed with 2×15 ml of MeOH (20-25° C.)
customdried on air

Sources & evidence

ORD record: ord-370cf6944fec4aaea716719aca1f5a39
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346751B2

Reaction notes

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