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

HRID 1699540Notes

Reaction equation

HRID 1699540 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-d69f99a51b38462e84cf43a96ceffb04
Source dataset
uspto-grants-2002_02
Patent number
USRE037556E1

Reaction notes

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