Lawesson's reagent → HCID 131718740, compound

HRID 1708230Notes

Reaction equation

HRID 1708230 reaction equation
[CH2:1]([C:8]1[CH:23]=[CH:22][C:11]([O:12][CH2:13][CH2:14][NH:15][C:16]([CH2:18][CH:19]2[CH2:21][CH2:20]2)=O)=[C:10]([Cl:24])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:34])=CC=1>C1(C)C=CC=CC=1>[CH2:1]([C:8]1[CH:23]=[CH:22][C:11]([O:12][CH2:13][CH2:14][NH:15][C:16](=[S:34])[CH2:18][CH:19]2[CH2:21][CH2:20]2)=[C:10]([Cl:24])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 131718741HCID 131718741, compound

Product 1

HCID 131718740HCID 131718740, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 500 mg (1.52 mmol) of N-[2-(4-benzyl-2-chlorophenoxy)ethyl]-cyclopropane carboxyamide, 614 mg (1.52 mmol) of a Lawesson's reagent and 20 ml of anhydrous toluene was refluxed by heating with stirring. After 20 minutes, the reaction mixture was cooled and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to give 487 mg of N-[2-(4-benzyl-2-chlorophenoxy)ethyl]-cyclopropane thiocarboxyamide as a colorless oily substance nD23.6 1.6041). After one week, the oily substance caked as a white solid (m.p. 90°-92° C. .

Workup

  1. temperaturewas refluxed
  2. temperatureby heating
  3. temperaturethe reaction mixture was cooled
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e9ab7cbb71744971bb148df1990fbab1
Source dataset
uspto-grants-1994_10
Patent number
US05356930

Reaction notes

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