Lawesson's reagent → HCID 59403050, compound

HRID 538603Notes

Reaction equation

HRID 538603 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([NH:11][C:12](=O)[CH2:13][O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:5]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:33])=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([NH:11][C:12](=[S:33])[CH2:13][O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:5]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 594027513-(2-Benzyloxy-acetylamino)-4-chloro-benzoic acid methyl ester

Product 1

HCID 59403050HCID 59403050, compoundYield 137.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To the solution of 3-(2-Benzyloxy-acetylamino)-4-chloro-benzoic acid methyl ester (1.70 g, 5.10 mmol) in 20 ml of toluene was added Lawesson's reagent (1.03 g, 2.50 mmol) and the reaction mixture was heated at 120° C. for 2 h. After the completion of the reaction mixture (TLC monitoring), the reaction mixture was evaporated to dryness under reduced pressure. The residue was purified by column chromatography on silica (60-120 M) using ethyl acetate/hexane (5:95) as the eluent to provide the title compound (1.20 g, 67%).

Workup

  1. customAfter the completion of the reaction mixture (TLC monitoring), the reaction mixture was evaporated to dryness under reduced pressure
  2. customThe residue was purified by column chromatography on silica (60-120 M)

Sources & evidence

ORD record
ord-36adf4a6bdd24fefb6a62af72d31a501
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

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