Lawesson's reagent → 2-bromo-2'-thioxo-6,7-dihydro-5H-spiro[benzo[b]thiophene-4,4'-imidazolidin]-5'-one

HRID 590527Notes

Reaction equation

[Br:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][C:10]3([C:14](=[O:15])[NH:13][C:12](=O)[NH:11]3)[C:4]=2[CH:3]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:26]2)=CC=1>O1CCOCC1>[Br:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][C:10]3([C:14](=[O:15])[NH:13][C:12](=[S:26])[NH:11]3)[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

2-Bromo-6,7-dihydro-5H-spiro[benzo[b]thiophene-4,4′-imidazolidine]-2′,5′-dione (0.5 g, 1.67 mmol) and 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide (Lawesson's reagent) (0.371 g, 0.91 mmol) were suspended in 1,4-dioxane (5 mL). The mixture was heated by microwave irradiation at 110° C. for 2×30 min. The solution was concentrated in vacuo and the crude residue purified on silica gel using ethyl acetate in 40-60 petroleum ether (1:1) to afford the title compound as a colourless solid (0.28 g, 53%).

Workup

concentrationThe solution was concentrated in vacuo
customthe crude residue purified on silica gel

Sources & evidence

ORD record: ord-840c475f24e146dc8c14d46e1b003c63
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233982B2

Reaction notes

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