3,4-Dimethoxybenzonitrile → 3,4-Dimethoxythiobenzamide

HRID 1699539Notes

Reaction equation

HRID 1699539 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:6]#[N:7].C(N)(=[S:15])C>Cl.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:6]([NH2:7])=[S:15]

Participants

4

Reactant 2

HCID 748423,4-DimethoxybenzonitrileHCID 2723949Thioacetamide

Product 1

HCID 27584903,4-DimethoxythiobenzamideYield 61.9%

Reagents, catalysts & solvents 1

HCID 10920465N,N-dimethylformamide;hydrochlorideSolvent

Conditions

Temperature
90 °C

Procedure

25 g of 3,4-dimethyoxybenzonitrile and 23 g of thioacetamide were dissolved in 120 ml of 10% hydrochloric acid-DMF. The solution was heated at 90° C. for 3 hours. The solution was further heated at 130° C. for 5 hours to conduct a reaction. The solvent was removed by distillation. The residue was washed twice with 100 ml of diethyl ether. Similar washing was conducted with 100 ml of water. The resulting crystals were collected by filtration and dried. Recrystallization from methanol was conducted to obtain 18.7 g of 3,4-dimethoxythiobenzamide as light brown columnar crystals.

Workup

  1. temperatureThe solution was further heated at 130° C. for 5 hours
  2. customa reaction
  3. customThe solvent was removed by distillation
  4. washThe residue was washed twice with 100 ml of diethyl ether
  5. washSimilar washing
  6. filtrationThe resulting crystals were collected by filtration
  7. customdried
  8. customRecrystallization from methanol

Sources & evidence

ORD record
ord-facaff1c299d4051adb3881fbf89b2e6
Source dataset
uspto-grants-2002_02
Patent number
USRE037556E1

Reaction notes

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