Water → HCID 85844986, compound

HRID 1179117Notes

Reaction equation

HRID 1179117 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[NH:11][C:12]([CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:29])=CC=1.O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[NH:11][C:12]([CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[S:29]

Participants

5

Reactant 3

HCID 962WaterHCID 87949Lawesson's reagentHCID 531821N-(2,5-dimethoxyphenyl)cyclohexanecarboxamide

Product 1

HCID 85844986HCID 85844986, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

1.46 g (5.54 mmol) of N-(2,5-dimethoxyphenyl)cyclohexanecarboxamide is put into solution in 40 ml of anhydrous toluene. The solution is taken to 100° C., and 3.34 g (8.26 mmol; 1.5 eq.) of Lawesson's reagent are added to the reaction medium which is then maintained under stirring at 100° C. for 4 hours. After returning to ambient temperature, the solution is poured into 50 ml of iced water and extracted using toluene. The organic phases are dried over magnesium sulphate and the solvent is evaporated off. The N-(2,5-dimethoxyphenyl)cyclohexanecarbothioamide is then purified by chromatography on a silica column (eluent: dichloromethane/heptane: 1/1 then 3/2). 1.26 g (yield=81%) of product is obtained in the form of yellow oil.

Workup

  1. customis taken to 100° C.
  2. temperatureis then maintained
  3. customAfter returning to ambient temperature
  4. extractionextracted
  5. dry with materialThe organic phases are dried over magnesium sulphate
  6. customthe solvent is evaporated off
  7. customThe N-(2,5-dimethoxyphenyl)cyclohexanecarbothioamide is then purified by chromatography on a silica column (eluent

Sources & evidence

ORD record
ord-74144ee1d01748d78edb39e6ff2f4f30
Source dataset
uspto-grants-2007_10
Patent number
US07279467B2

Reaction notes

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