p-nitrophenol sodium salt → 2-[(4-Nitrophenoxy)methyl]-1H-1lambda~6~,2-benzothiazole-1,1,3(2H)-trione

HRID 266439

Reaction equation

Cl[CH2:2][N:3]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[S:4]1(=[O:6])=[O:5].[N+:15]([C:18]1[CH:24]=[CH:23][C:21]([O-:22])=[CH:20][CH:19]=1)([O-:17])=[O:16].[Na+]>C1COCC1>[N+:15]([C:18]1[CH:24]=[CH:23][C:21]([O:22][CH2:2][N:3]2[C:13](=[O:14])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:4]2(=[O:6])=[O:5])=[CH:20][CH:19]=1)([O-:17])=[O:16]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2-(chloromethyl) saccharin (3 g, 12.9 mmol) and sodium p-nitrophenoxide (2.55 g, 12.9 mmol) in THF (50 ml) was heated overnight at 50° C. and then refluxed for 45 minutes. The reaction mixture was cooled, poured into a dilute sodium bicarbonate/ice solution and extracted twice with ethyl acetate. The combined organic extracts were washed with sodium bicarbonate solution and water, dried (Na2SO4), and taken to dryness in vacuo. Chromatography (silica gel; MDC) afforded an oil that was crystallized from hot cyclohexane/ether. The resultant solid was recrystallized from ethanol to afford 0.92 g of 2-(4-nitrophenoxymethyl)-saccharin as white shiny platelets, mp 162°-164° C. 1H nmr (90 MHz, CDCl3, DMSO-d6):5.95 (2H, s). FDMS m/e 334 (M+).

Workup

temperaturerefluxed for 45 minutes
temperatureThe reaction mixture was cooled
extractionextracted twice with ethyl acetate
washThe combined organic extracts were washed with sodium bicarbonate solution and water
dry with materialdried (Na2SO4)
customChromatography (silica gel; MDC) afforded an oil that
customwas crystallized from hot cyclohexane/ether
customThe resultant solid was recrystallized from ethanol

Sources & evidence

ORD record: ord-d7ea0a1b46ce450e9e071c7e102e50cb
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05650422

Linked notes

Loading…