Toluene → Benzamide, thio-3,4,5-trimethoxy-

HRID 992983Notes

Reaction equation

HRID 992983 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6]([NH2:8])=O.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:25]2)=CC=1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6](=[S:25])[NH2:8]

Participants

5

Reactant 3

HCID 1140TolueneHCID 18334Benzamide, 3,4,5-trimethoxy-HCID 87949Lawesson's reagent

Product 1

HCID 3033195Benzamide, thio-3,4,5-trimethoxy-

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

3,4,5-Trimethoxybenzamide (5.0 g) and 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (5.24 g) were added to toluene, and the mixture was stirred at 70° C. After 5 hours, the reaction mixture was cooled back to room temperature, diluted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was then purified by column chromatography on silica gel (hexane:ethyl acetate=1:1 to 1:2) to obtain yellow crystals, and the crystals were further recrystallized from ethyl acetate-hexane to obtain the title compound.

Workup

  1. temperaturethe reaction mixture was cooled back to room temperature
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was then purified by column chromatography on silica gel (hexane:ethyl acetate=1:1 to 1:2)
  6. customto obtain yellow crystals
  7. customthe crystals were further recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-be5153d391294b19856519af253a945d
Source dataset
uspto-grants-2002_10
Patent number
US06472386B1

Reaction notes

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