Lawesson's reagent → HCID 19884271, compound

HRID 846869Notes

Reaction equation

HRID 846869 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[N:13]1[C:17](=O)[N:16]([CH:19]([CH3:21])[CH3:20])[N:15]=[N:14]1)([CH3:3])[CH3:2].COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:31]2)=CC=1>C1(C)C=CC=CC=1>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[N:13]1[C:17](=[S:31])[N:16]([CH:19]([CH3:21])[CH3:20])[N:15]=[N:14]1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 19884287HCID 19884287, compound

Product 1

HCID 19884271HCID 19884271, compoundYield 109.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5.6 g of 1-(2,6-diisopropylphenyl)-4-isopropyl-5-oxo-2-tetrazoline and 5.1 g of 2,4-bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (Lawesson's reagent) are heated at reflux for 24 hours in 60 ml of dry toluene. After evaporating off the solvent, the residue is purified by chromatography on 500 g of silica gel with hexane/ethyl acetate (19:1) as eluant. Crystallisation from hexane yields 4.2 g of 1-(2,6-diisopropylphenyl)-4-isopropyl-5-thioxo-2-tetrazoline in the form of colourless crystals, m.p. 109°-111° C.

Workup

  1. temperatureare heated
  2. customAfter evaporating off the solvent
  3. customthe residue is purified by chromatography on 500 g of silica gel with hexane/ethyl acetate (19:1) as eluant
  4. customCrystallisation from hexane

Sources & evidence

ORD record
ord-7bb4668cd9954e5abd6087295fe476ac
Source dataset
uspto-grants-1992_08
Patent number
US05138068

Reaction notes

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