Lawesson's reagent → HCID 136060824, compound

HRID 1851546Notes

Reaction equation

[CH3:1][N:2]([S:24]([C:27]1[S:28][CH:29]=[CH:30][CH:31]=1)(=[O:26])=[O:25])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]([NH:14][NH:15][C:16](=O)[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=O)=[CH:8]2.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:41])=CC=1>O1CCCC1>[CH3:1][N:2]([S:24]([C:27]1[S:28][CH:29]=[CH:30][CH:31]=1)(=[O:26])=[O:25])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:41][C:16]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:15][N:14]=1)=[CH:8]2

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of ethyl 3-[2-({7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}carbonyl)hydrazino]-3-oxopropanoate (0.96 g), Lawesson's reagent (0.97 g) and tetrahydrofuran (20 mL) was stirred at 50° C. for 2 hr. The reaction mixture was concentrated, and the residue was subjected to silica gel column chromatography, and the title compound (0.70 g, yield 71%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point 201-202° C.

Workup

concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record: ord-4148e83f580a4401bde623dc1ec96c8c
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957070B2

Reaction notes

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