Thioacetamide → 3,4-Diethoxybenzene-1-carbothioamide

HRID 1370577

Reaction equation

HRID 1370577 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:17])C>Cl.CN(C=O)C>[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])=[S:17])[CH3:2]

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 129461903,4-Diethoxybenzonitrile

Product 1

HCID 77452503,4-Diethoxybenzene-1-carbothioamideYield 63.5%

Reagents, catalysts & solvents 1

HCID 10920465N,N-dimethylformamide;hydrochlorideSolvent

Procedure

A solution of 29 g of 3,4-diethoxybenzonitrile and 23 g of thioacetamide in 120 ml of 10% hydrochloric acid-DMF was stirred at 90° C. for 3 hours and then 130° C. for 5 hours. After evaporation of the solvent, the residue was washed with diethyl ether (2×100 ml) and water (2×100 ml). The resulting crystals were collected by filtration and dried to obtain 21.7 g of 3,4-diethoxythiobenzamide.

Workup

  1. customAfter evaporation of the solvent
  2. washthe residue was washed with diethyl ether (2×100 ml) and water (2×100 ml)
  3. filtrationThe resulting crystals were collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-ddc63047cca2436481bdc6795ef376f5
Source dataset
uspto-grants-2003_06
Patent number
US06583163B2

Linked notes

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