Lawesson's reagent → 4-Methoxy-2'-methoxybenzothioanilide

HRID 1165478Notes

Reaction equation

HRID 1165478 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])=O)=[CH:5][CH:4]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:29])=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([C:7](=[S:29])[NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 3460502',4-Dimethoxybenzanilide

Product 1

HCID 101073544-Methoxy-2'-methoxybenzothioanilideYield 153.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Methoxy-2'-methoxybenzanilide (29.5 g) [Bull. Soc. Chim. France, 1964, (5), 924-935] was dissolved in 150 ml of toluene, and 25.6 g of Lawesson's reagent was added. The mixture was refluxed for 4.5 hours. After the reaction, the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography [eluted with cyclohexane/ethyl acetate (7/1, v/v)] to give 26.5 g of 4-methoxy-2'-methoxybenzothioanilide.

Workup

  1. temperatureThe mixture was refluxed for 4.5 hours
  2. customAfter the reaction
  3. customthe solvent was evaporated under reduced pressure
  4. washeluted with cyclohexane/ethyl acetate (7/1

Sources & evidence

ORD record
ord-94baf0ff19ed435c9ddb1361e448ac62
Source dataset
uspto-grants-1990_03
Patent number
US04910211

Reaction notes

Loading…