Lawesson's reagent → 2-(3'-Nitrophenyl)-5-(p-tolyl)-1,3,4-thiadiazole
Reaction equation
[CH3:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([NH:8][NH:9][C:10](=O)[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)=O)=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1>C1C=CC=CC=1>[N+:17]([C:13]1[CH:12]=[C:11]([C:10]2[S:32][C:6]([C:5]3[CH:21]=[CH:22][C:2]([CH3:1])=[CH:3][CH:4]=3)=[N:8][N:9]=2)[CH:16]=[CH:15][CH:14]=1)([O-:19])=[O:18]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 1-[(4-methyl)benzoyl]-2-(3-nitrobenzoyl)hydrazine (1.40 g, 4.68 mmol) and Lawesson's Reagent (0.95 g, 2.34 mmol) in benzene (25 ml) is slowly heated to 60° C. After 3 hours the solution is concentrated, quenched with 35 ml of water and heated to reflux for 12 hours. The mixture is then cooled to room temperature and the precpitate is collected by filtration. The precipitate is then taken up in chloroform (100 ml) and the insoluble portion is removed by filtration. The filtrate is then dried over MgSO4 and concentrated to yield 2-(3′-nitrophenyl)-5-(p-tolyl)-1,3,4-thiadiazole as a pale yellow solid. (0.67 g, 48%). 1H NMR (CDCl3): δ 2.45 (s, 3H), 7.35 (d, 2H), 7.73 (t, 1H), 7.92 (d, 2H), 8.38 (t, 2H), 8.81 (s, 1H).
Workup
- concentrationAfter 3 hours the solution is concentrated
- customquenched with 35 ml of water
- temperatureheated
- temperatureto reflux for 12 hours
- temperatureThe mixture is then cooled to room temperature
- filtrationthe precpitate is collected by filtration
- customthe insoluble portion is removed by filtration
- dry with materialThe filtrate is then dried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-5381c4234f7b446d91e74716ea5ad103
- Source dataset
- uspto-grants-2001_08
- Patent number
- US06281217B1
Reaction notes
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