Lawesson's reagent → Ethyl 5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-1,3,4-thiadiazole-2-carboxylate

HRID 1881930Notes

Reaction equation

HRID 1881930 reaction equation
[Si:1]([O:18][CH2:19][C:20]([NH:22][NH:23][C:24](=O)[C:25]([O:27][CH2:28][CH3:29])=[O:26])=O)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[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:40])=CC=1>O1CCCC1>[Si:1]([O:18][CH2:19][C:20]1[S:40][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[N:23][N:22]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 59331270Ethyl [2-({[tert-butyl(diphenyl)silyl]oxy}acetyl)hydrazino](oxo)acetate

Product 1

HCID 59331459Ethyl 5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-1,3,4-thiadiazole-2-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl [2-({[tert-butyl(diphenyl)silyl]oxy}acetyl)hydrazino](oxo)acetate (3.20 g) in tetrahydrofuran (30 mL) was added Lawesson's reagent (3.02 g), and the mixture was stirred at room temperature for 24 hr. The reaction mixture was concentrated, and the residue was subjected to silica gel column chromatography, and the title compound (3.05 g, yield 96%) was obtained as a colorless amorphous solid from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-103120adf4454334b9f7ae51b50e027e
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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