Phosphorus sulfide (P2S5) → Benzamide, thio-3,4,5-trimethoxy-

HRID 1421945Notes

Reaction equation

HRID 1421945 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.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:17]>C1C=CC=CC=1>[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])=[S:17]

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 18334Benzamide, 3,4,5-trimethoxy-

Product 1

HCID 3033195Benzamide, thio-3,4,5-trimethoxy-Yield 122.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

500 mg of 3,4,5-trimethoxybenzamide was suspended in 15 ml of benzene. Thereto was added 526 mg of phosphorus pentasulfide. The mixture was refluxed for 30 minutes with heating. The solvent was removed by distillation. To the residue were added 5 ml of 10% sodium hydroxide and 5 ml of water. The mixture was stirred for 30 minutes. The reaction mixture was filtered, and the resulting solid was washed with small amounts of water and ethanol and dried to obtain 330 mg of 3,4,5-trimethoxythiobenzamide as a yellow powder.

Workup

  1. temperatureThe mixture was refluxed for 30 minutes
  2. temperaturewith heating
  3. customThe solvent was removed by distillation
  4. additionTo the residue were added 5 ml of 10% sodium hydroxide and 5 ml of water
  5. filtrationThe reaction mixture was filtered
  6. washthe resulting solid was washed with small amounts of water and ethanol
  7. customdried

Sources & evidence

ORD record
ord-53dd710709b441e891cbfd7ed528bf34
Source dataset
uspto-grants-2000_06
Patent number
US06080764

Reaction notes

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