1,3,2,4-Dithiadiphosphetane, 2,4-bis(methylthio)-, 2,4-disulfide → (S)-methyl 3,4-dihydro-2,8-diisopropyl-3-thioxo-2H-1,4-benzoxazine-4-acetate

HRID 622371Notes

Reaction equation

[CH:1]([C@H:4]1[C:9](=O)[N:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:7]2[CH:16]=[CH:17][CH:18]=[C:19]([CH:20]([CH3:22])[CH3:21])[C:6]=2[O:5]1)([CH3:3])[CH3:2].C[S:24]P1(=S)SP(=S)(SC)S1>C1(C)C=CC=CC=1>[CH:1]([C@H:4]1[C:9](=[S:24])[N:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:7]2[CH:16]=[CH:17][CH:18]=[C:19]([CH:20]([CH3:22])[CH3:21])[C:6]=2[O:5]1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of (S)-methyl 3,4-dihydro-2,8-diisopropyl-3-oxo-2H-1,4-benzoxazine-4-acetate (3.05 g), 2,4-bis (methylthio)-1,3,2,4-dithiadiphosphetan-2,4-disulfide (Davy reagent methyl)(2.84 g) and toluene (60 ml) was stirred at 50° C. for 64 hours. The insoluble material was filtered off and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (100 g) using hexane-ethyl ether (85:15, v/v) as the eluent to yield (S)-methyl 3,4-dihydro-2,8-diisopropyl-3-thioxo-2H-1,4-benzoxazine-4-acetate as an oil (3.00 g).

Workup

filtrationThe insoluble material was filtered off
concentrationthe filtrate was concentrated
customThe residue was purified by column chromatography on silica gel (100 g)

Sources & evidence

ORD record: ord-197c87abe532419fa93d5c5c3b370478
Source dataset: uspto-grants-1988_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04771050

Reaction notes

Loading…