Thiosemicarbazide → 5-[(4-Methoxyphenyl)methyl]-1,3,4-thiadiazol-2-amine
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](Cl)=O)=[CH:5][CH:4]=1.[NH2:13][NH:14][C:15]([NH2:17])=[S:16]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]2[S:16][C:15]([NH2:17])=[N:14][N:13]=2)=[CH:5][CH:4]=1Participants
3
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 2-(4-methoxyphenyl)acetyl chloride (88a, 3.05 g, 16.5 mmol), and thiosemicarbazide (1.37 g, 15.0 mmol) were heated to 60° C. for 3.0 hours. The reaction mixture was then cooled to room temperature, quenched with water and extracted with ethyl acetate. The organic layer was washed with brine and 50% NaOH(aq), dried over. MgSO4(s), and concentrated under reduced pressure to give 5-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine (88b).
Workup
- temperatureThe reaction mixture was then cooled to room temperature