Tetrahydrofuran → 3-(4-Nitrobenzoyl)-1,3-thiazolidine-2-thione

HRID 1632248Notes

Reaction equation

[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].O1CCCC1.[S:18]1[CH2:22][CH2:21][NH:20][C:19]1=[S:23]>C(N(CC)CC)C>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([N:20]2[CH2:21][CH2:22][S:18][C:19]2=[S:23])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 4-nitrobenzoyl chloride (3.1 g) and tetrahydrofuran (50 ml) were added 1,3-thiazolidine-2-thione (2.0 g) and triethyl amine (2.5 g). The mixture was stirred at 50° C. for 30 minutes under nitrogen atmosphere. The reaction mixture was filtered and the solvent was removed at a reduced pressure. To the residue was added water, and the solution is extracted with dichloromethane. The extract was washed with a saturated aqueous solution of sodium chloride and dried with use of Glauber's salt. The solvent was distilled off and the resulting crystals were purified by silica gel column chromatography (developer: dichloromethane) and recrystallized from dichloromethane to obtain 3.3 g of the desired compound as yellow needle crystals (yield 82.5%).

Workup

filtrationThe reaction mixture was filtered
customthe solvent was removed at a reduced pressure
additionTo the residue was added water
extractionthe solution is extracted with dichloromethane
washThe extract was washed with a saturated aqueous solution of sodium chloride
dry with materialdried with use of Glauber's salt
distillationThe solvent was distilled off
customthe resulting crystals were purified by silica gel column chromatography (developer: dichloromethane)
customrecrystallized from dichloromethane

Sources & evidence

ORD record: ord-c4d3668f304a4101990443742a0e5fe2
Source dataset: uspto-grants-1984_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04474814

Reaction notes

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