Lawesson's reagent → 12-Methoxydodecanethioamide

HRID 1600423Notes

Reaction equation

HRID 1600423 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH2:16])=O.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:26]2)=CC=1>O1CCCC1>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[S:26])[NH2:16]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 983750412-Methoxydodecanamide

Product 1

HCID 1961177612-MethoxydodecanethioamideYield 127.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the title product from Example 12 (1.0 g, 5 mmol) in 70 mL of anhydrous tetrahydrofuran was added 2,4-bis (4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide [Lawesson's Reagent] (1.0 g, 2 mmol). After stirring at room temperature for 1 day, the solvent was removed by rotary evaporator and the resulting residue waspurified by chromatography on silica gel using 30-70 ethyl acetate-hexane as eluant to give the title compound (625 mg) as a white solid, m.p. 86.8°-89.2° C. (DSC). The structure was supported by NMR, infrared spectroscopy, elemental analysis, and mass spectroscopy.

Workup

  1. customthe solvent was removed by rotary evaporator

Sources & evidence

ORD record
ord-686c5dd0ce454f639ddb0d75c9bf629e
Source dataset
uspto-grants-1998_04
Patent number
US05744631

Reaction notes

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