Water → 2',3'-Diamino-3,4,4',5-tetramethoxy-(Z)-stilbene

HRID 131094Notes

Reaction equation

[N+:1]([C:4]1[C:23]([N+:24]([O-])=O)=[C:22]([O:27][CH3:28])[CH:21]=[CH:20][C:5]=1/[CH:6]=[CH:7]\[C:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=1)([O-])=O.S([O-])([O-])(=O)=S.[Na+].[Na+].O>CC(C)=O.O>[NH2:1][C:4]1[C:23]([NH2:24])=[C:22]([O:27][CH3:28])[CH:21]=[CH:20][C:5]=1/[CH:6]=[CH:7]\[C:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A well-stirred solution of 2′,3′-Dinitro-3,4,4′,5-tetramethoxy-(Z)-stilbene (0.422 g, 1.08 mmol) in a mixture of acetone-water (2:1) was heated to 50° C. Then sodium thiosulfate (1.88 g, 10.81 mmol, 10.0 equiv) was added and the reaction mixture was heated to reflux for 6 hours. The reaction was cooled to room temperature and water was added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (4×25 mL). The combined organic layer were washed with brine, dried over Na2SO4 and concentrated in vacuo. The mixture was then subjected to preparative TLC to give the 2′,3′-Diamino-3,4,4′,5-tetramethoxy-(Z)-stilbene.

Workup

temperaturethe reaction mixture was heated
temperatureto reflux for 6 hours
temperatureThe reaction was cooled to room temperature
customThe organic layer was separated
extractionthe aqueous layer was extracted with ethyl acetate (4×25 mL)
washThe combined organic layer were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-c5ab9edf7c63427fb56546fa8e89e693
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384925B2

Reaction notes

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