Lawesson's reagent → 2-(3-iodo-1-tosyl-1H-indol-5-yl)-5-phenyl-1,3,4-thiadiazole

HRID 634238Notes

Reaction equation

[C:1]([NH:9][NH:10][C:11]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[N:18]([S:22]([C:25]1[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=1)(=[O:24])=[O:23])[CH:17]=[C:16]2[I:32])=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:42])=CC=1>O1CCOCC1>[I:32][C:16]1[C:15]2[C:19](=[CH:20][CH:21]=[C:13]([C:11]3[S:42][C:1]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[N:9][N:10]=3)[CH:14]=2)[N:18]([S:22]([C:25]2[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH:17]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a suspension of N′-benzoyl-3-iodo-1-tosyl-1H-indole-5-carbohydrazide (1.29 g, 2.31 mmol) in dioxane (24 mL) at RT was added Lawesson's Reagent (1.40 g, 3.46 mmol) (Aldrich). The solution was heated to 110° C. for 3 h. The mixture was concentrated and the residue was purified with flash chromatography (eluting with 0-60% EtOAc in Hex) to give 2-(3-iodo-1-tosyl-1H-indol-5-yl)-5-phenyl-1,3,4-thiadiazole (518 mg, 40%) as a light yellow-orange crystalline solid after washing with Et2O. MS (ESI, pos. ion) m/z: 557.9 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 7.96-8.10 (5H, m), 7.81 (2H, d, J=8.4 Hz), 7.77 (1H, s), 7.48-7.55 (3H, m), 7.28 (2H, d, J=8.2 Hz), 2.37 (3H, s).

Workup

concentrationThe mixture was concentrated
customthe residue was purified with flash chromatography (eluting with 0-60% EtOAc in Hex)

Sources & evidence

ORD record: ord-8d71c3b4ccd74262bf6958a9762792cc
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321756B2

Reaction notes

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