Lawesson's reagent → HCID 19768613, compound

HRID 1085828Notes

Reaction equation

HRID 1085828 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=O)#[N:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:30])=CC=1>C1(C)C(C)=CC=CC=1>[C:1]([C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[S:30])#[N:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 19768581HCID 19768581, compound

Product 1

HCID 19768613HCID 19768613, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

In an analogous manner to that described in Example 1(B). 8.9 g (33.3 mmol) of methyl 3-[(3-cyanobenzyl)oxy]benzoate were heated to reflux for 17 hours with 13.5 g (33.4 mmol) of Lawesson reagent in xylene and thereafter chromatographed on silica gel. Elution with an 8:2 and 7:3 mixture of hexane and methylene chloride yielded 7.6 g (65.8%) of O-methyl 3-[(3-cyanobenzyl)oxy]thiobenzoate as a yellow oil which gradually crystallized upon standing.

Workup

  1. customchromatographed on silica gel
  2. washElution
  3. additionwith an 8:2 and 7:3 mixture of hexane and methylene chloride

Sources & evidence

ORD record
ord-dc53b5d396ed441bafd69e8fbdcbdf81
Source dataset
uspto-grants-1991_04
Patent number
US05011849

Reaction notes

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