Lawesson's reagent → 4-Chloro-2-methoxythiobenzamide

HRID 1498903Notes

Reaction equation

HRID 1498903 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=O)=[C:4]([O:11][CH3:12])[CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:22])=CC=1.C(=O)(O)[O-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[S:22])=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

5

Reactant 3

HCID 87949Lawesson's reagentHCID 516892Sodium BicarbonateHCID 19741766HCID 19741766, compound

Product 1

HCID 630943604-Chloro-2-methoxythiobenzamideYield 129.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In tetrahydrofuran (100 ml), 4-chloro-2-methoxybenzamide (9.40 g, 50.6 mmol) prepared in the Step 7-1-1 and Lawesson's reagent (10.2 g, 25.3 mmol) were suspended, and the suspension was heated under reflux for 2 hours. After the suspension was allowed to cool, a saturated sodium bicarbonate solution was added to the suspension to stop the reaction. Then the reaction mixture was subjected to extraction with ethyl acetate, and the extract was dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to give the title compound (6.63 g, 65%) as a yellow powder.

Workup

  1. temperaturethe suspension was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureto cool
  4. customthe reaction
  5. extractionThen the reaction mixture was subjected to extraction with ethyl acetate
  6. dry with materialthe extract was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe concentrate was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-f325de120afe492fab11fab3b79ce444
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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