Lawesson's reagent → N-cyclohexylmethyl-4-(2-propynyloxy)-3,5-dimethoxybenzenethioamide

HRID 601991Notes

Reaction equation

HRID 601991 reaction equation
[CH:1]1([CH2:7][NH:8][C:9](=O)[C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH2:19][C:20]#[CH:21])=[C:12]([O:22][CH3:23])[CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:34])=CC=1>C1(C)C=CC=CC=1>[CH:1]1([CH2:7][NH:8][C:9]([C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH2:19][C:20]#[CH:21])=[C:12]([O:22][CH3:23])[CH:11]=2)=[S:34])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 57445670N-cyclohexylmethyl-4-(2-propynyloxy)-3,5-dimethoxybenzamide

Product 1

HCID 57701142N-cyclohexylmethyl-4-(2-propynyloxy)-3,5-dimethoxybenzenethioamideYield 63.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 30 ml of toluene were added 1.2 g of N-cyclohexylmethyl-4-(2-propynyloxy)-3,5-dimethoxybenzamide and 1.8 g of Lawesson's Reagent and the mixture obtained was heated under reflux for 2 hours. Then, the reaction mixture was concentrated. The residue was subjected to silica gel column chromatography to obtain 0.80 g of N-cyclohexylmethyl-4-(2-propynyloxy)-3,5-dimethoxybenzenethioamide (hereinafter, described as the compound 33 of the present invention) represented by the formula:

Workup

  1. customthe mixture obtained
  2. temperaturewas heated
  3. temperatureunder reflux for 2 hours
  4. concentrationThen, the reaction mixture was concentrated

Sources & evidence

ORD record
ord-49e25edb2a8b4bfa9c7135bcc4303684
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Reaction notes

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