Diethyl Ether → O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

HRID 1253451Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.[NH2:10][O:11][S:12]([C:15]1[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=1[CH3:23])(=[O:14])=[O:13].CCOCC>ClCCl>[NH2:10][O:11][S:12]([C:15]1[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=1[CH3:23])(=[O:13])=[O:14].[CH3:21][C:20]1[CH:19]=[C:18]([CH3:22])[CH:17]=[C:16]([CH3:23])[C:15]=1[S:12]([O-:14])(=[O:13])=[O:11].[NH2:10][N+:4]1[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(Adapted from: Miki, Y. et. al.; Heterocycles 1996, 43, 2249-2256; 2-[(aminooxy)sulfonyl]-1,3,5-trimethylbenzene was prepared using the procedure described in Krause, J. G. Synthesis, 1972, 3, 140). A solution of 3-bromo-5-methoxypyridine (8.72 g, 46.4 mmol) in dichloromethane (93 ml) was cooled to 0° C. A solution of 2-[(aminooxy)sulfonyl]-1,3,5-trimethylbenzene (13.31 g, 46.4 mmol) in dichloromethane (93 ml) was added in a steady stream via canula and the mixture was allowed to stir for 1 h at 0° C. At this time, 460 mL of ether was added dropwise via addition funnel over 5 minutes. The precipitated solid was collected via filtration, and washed with cold ether. The solid was placed under vacuum for 30 minutes to afford 1-amino-3-bromo-5-methoxypyridinium 2,4,6-trimethylbenzenesulfonate as a colorless solid.

Workup

customSynthesis, 1972, 3, 140)
filtrationThe precipitated solid was collected via filtration
washwashed with cold ether
waitThe solid was placed under vacuum for 30 minutes

Sources & evidence

ORD record: ord-f85c168eba1148ee8758e08e79a61452
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455477B2

Reaction notes

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