Thioacetamide → 3,4-Diethoxybenzamide

HRID 1683776

Reaction equation

HRID 1683776 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[C:7]#[N:8])[CH3:2].C(N)(=S)C.Cl.CN(C)C=[O:23]>>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[C:7]([NH2:8])=[O:23])[CH3:2]

Participants

4

Reactant 3

HCID 2723949ThioacetamideHCID 10920465N,N-dimethylformamide;hydrochlorideHCID 129461903,4-Diethoxybenzonitrile

Product 1

HCID 3403423,4-Diethoxybenzamide

Conditions

Temperature
130 °C

Procedure

In 120 ml of 10% hydrochloric acid-dimethylformamide were dissolved 29 g of 3,4-diethoxybenzonitrile and 23 g of thioacetamide. The solution was heated at 90° C. for 3 hours and further at 130° C. for 5 hours to conduct a reaction. The reaction mixture was subjected to distillation to remove the solvent. The residue was washed twice with 100 ml of diethyl ether, followed by washing with 100 ml of water. The resulting crystals were collected by filtration and dried to obtain 21.7 g of 3,4-diethoxybenzamide.

Workup

  1. customa reaction
  2. distillationThe reaction mixture was subjected to distillation
  3. customto remove the solvent
  4. washThe residue was washed twice with 100 ml of diethyl ether
  5. washby washing with 100 ml of water
  6. filtrationThe resulting crystals were collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-2e74b48555d0458f88c4a448e6027f25
Source dataset
uspto-grants-1997_06
Patent number
US05639770

Linked notes

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