Pyridine → N-[(4-Methoxyphenyl)carbonothioyl]acetamide

HRID 353963

Reaction equation

HRID 353963 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([NH2:13])=[S:12])=[CH:9][CH:8]=1.N1C=CC=CC=1>CC(C)=O>[CH3:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([NH:13][C:1](=[O:3])[CH3:2])=[S:12])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 7368274-Methoxybenzenecarbothioamide

Product 1

HCID 13835614N-[(4-Methoxyphenyl)carbonothioyl]acetamideYield 72.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of acetyl chloride (4.69 g, 59.8 mmol) in acetone (20 mL) was added dropwise to a solution of 4-methoxythiobenzamide (5.00 g, 29.9 mmol) and pyridine (4.76 g, 60.1 mmol) in acetone (30 mL). The reaction mixture was heated to reflux for 30 min then poured onto ice water. The resulting precipitate was isolated via filtration and dried under vacuum overnight to provide a light yellow/orange solid (4.52 g, 72%). 1H NMR (400 MHz, CDCl3) δ2.56 (s, 3H), 3.87 (s, 3H), 6.89 (dd, J=6.9, 2.0 Hz, 2H), (dd, J=6.9, 2.0 Hz, 2H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 30 min
  3. additionthen poured onto ice water
  4. customThe resulting precipitate was isolated via filtration
  5. customdried under vacuum overnight

Sources & evidence

ORD record
ord-a446000c981f4df8af9eebcc520453b9
Source dataset
uspto-grants-2004_06
Patent number
US06756372B2

Linked notes

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