Lawesson's reagent → HCID 59488854, compound

HRID 1960165Notes

Reaction equation

HRID 1960165 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=O)[C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([N+:24]([O-:26])=[O:25])[CH:18]=2)=[CH:11][CH:10]=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:37])=CC=1>O1CCOCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[S:37])[C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([N+:24]([O-:26])=[O:25])[CH:18]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 1379395ST50696295

Product 1

HCID 59488854HCID 59488854, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N-(4-Benzyloxy-phenyl)-4-chloro-3-nitro-benzamide (19.15 g, 50 mmol), Lawesson reagent (11 g, 27 mmol, commercially available) and dioxane (150 ml) were stirred together and heated under reflux for 4 h. When no more starting amide was present, as showed by TLC, the reaction mixture was cooled and the solvent removed under reduced pressure. The crude product was dissolved in minimum boiling toluene to recrystallise. The purified product was filtered and washed with cold toluene and cold hexane to give the thioamide, in 77% yield.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 h
  3. temperaturethe reaction mixture was cooled
  4. customthe solvent removed under reduced pressure
  5. dissolutionThe crude product was dissolved in minimum
  6. customto recrystallise
  7. filtrationThe purified product was filtered
  8. washwashed with cold toluene and cold hexane

Sources & evidence

ORD record
ord-9dbad1cb75e149959be34b8766ff9d55
Source dataset
uspto-grants-2013_04
Patent number
US08410312B2

Reaction notes

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