Lawesson's reagent → 4-Chloro-N-(4-(methylthio)phenyl)benzothioamide

HRID 1896779Notes

Reaction equation

HRID 1896779 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15][CH3:16])=[CH:11][CH:10]=2)=O)=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:28])=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6](=[S:28])[NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15][CH3:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 3064824-Chloro-N-[4-(methylthio)phenyl]benzamide

Product 1

HCID 576174804-Chloro-N-(4-(methylthio)phenyl)benzothioamideYield 79.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 4-chloro-N-(4-(methylthio)phenyl)benzamide (1 g, 3.60 mmol) and Lawesson's reagent (875 mg, 2.16 mmol) in toluene (25 mL) was heated to 11 0° C. for 16 h. After cooling, toluene was removed in vacuo and the resulting solid was purified by column chromatography eluting using a gradient (hexanes to ethyl acetate/hexanes 30:70 v/v) to afford 503 mg (48%) of the title compound.

Workup

  1. temperatureAfter cooling
  2. customtoluene was removed in vacuo
  3. customthe resulting solid was purified by column chromatography
  4. washeluting

Sources & evidence

ORD record
ord-272fea2a134049e38dc4500f14db7b95
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

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