Toluene → Methyl-2-methoxy-5-benzthioamido-benzoate

HRID 840605Notes

Reaction equation

HRID 840605 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([NH:10][C:11](=O)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:5]=1[O:19][CH3:20].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:31])=CC=1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([NH:10][C:11](=[S:31])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:5]=1[O:19][CH3:20]

Participants

5

Reactant 3

HCID 1140TolueneHCID 87949Lawesson's reagentHCID 22620052Methyl-2-methoxy-5-benzamidobenzoate

Product 1

HCID 86753484Methyl-2-methoxy-5-benzthioamido-benzoateYield 89.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 2 liter round bottom flask was charged with 15.7 grams (55 mmol) methyl-2-methoxy-5-benzamidobenzoate and 22.2 grams (55 mmol) of Lawesson's reagent followed by 500 mL of toluene. The reaction mixture was heated under reflux for 1.5 hours. The mixture was diluted with 500 mL of ethyl acetate, and washed with 250 mL of saturated aqueous bicarbonate solution, followed by washes with water and brine. The organic layer was dried over sodium sulfate, filtered and evaporated. The residue was chromatographed on silica eluting with 96/4 methylene chloride-ether. There was obtained 14.8 grams (89%) of desired material.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. washwashed with 250 mL of saturated aqueous bicarbonate solution
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was chromatographed on silica eluting with 96/4 methylene chloride-ether

Sources & evidence

ORD record
ord-8fb6b0a3f53c4d74a52d9432e7925bc7
Source dataset
uspto-grants-2002_04
Patent number
US06369074B1

Reaction notes

Loading…