Lawesson's reagent → HCID 131718740, compound

HRID 2380090Notes

Reaction equation

HRID 2380090 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-102e6aa2f6724e12862e6a94a0792e8b
Source dataset
uspto-grants-1994_11
Patent number
US05364966

Reaction notes

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