Hexane → Ethyl alpha-nitro-9H-thioxanthene-9-acetate

HRID 2399625Notes

Reaction equation

O[CH:2]1[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[N+:16]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])([O-:18])=[O:17].CCCCCC.[OH-].[K+]>O.C(O)C.CC(O)C>[N+:16]([CH:19]([CH:2]1[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:20]([O:22][CH2:23][CH3:24])=[O:21])([O-:18])=[O:17]

Participants

Conditions

Temperature: 100 °C

Procedure

Crude 9-hydroxythioxanthene (9.58 g, 45 mmol) is mixed with ethyl nitroacetate (5.5 mL, 49 mmol) and heated at 100° C. for 1 hour. TLC (SiO2, hexane:2-propanol/3:l) after 45 minutes shows no starting material. The cooled reaction mixture is treated with 100 mL of ethanol and 39 mL of 1.25M ethanolic potassium hydroxide solution. Ethanol is stripped and the residue taken up in water and extracted with diethyl ether. The aqueous layer is acidified to pH 2 to 3 with 85% phosphoric acid solution and refrigerated overnight. A crystalline solid is collected by filtration and dried at 50° C./10 mm Hg. A total of 8.4 g of the title compound is collected in three crops; mp 111°-115° C.

Workup

customThe cooled reaction mixture
extractionextracted with diethyl ether
filtrationA crystalline solid is collected by filtration
customdried at 50° C./10 mm Hg
customA total of 8.4 g of the title compound is collected in three crops

Sources & evidence

ORD record: ord-c65b29c2570c49998e2fdebbfdbf0651
Source dataset: uspto-grants-1995_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05449778

Reaction notes

Loading…