Lawesson's reagent → 2-(3'-Nitrophenyl)-5-(p-tolyl)-1,3,4-thiadiazole

HRID 843599Notes

Reaction equation

HRID 843599 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

HCID 87949Lawesson's reagentHCID 4506110N'-[(4-methylphenyl)carbonyl]-3-nitrobenzohydrazide

Product 1

HCID 226110572-(3'-Nitrophenyl)-5-(p-tolyl)-1,3,4-thiadiazole

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

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%).

Workup

  1. concentrationAfter 3 hours the solution is concentrated
  2. customquenched with 35 ml of water
  3. temperatureheated
  4. temperatureto reflux for 12 hours
  5. temperatureThe mixture is then cooled to room temperature
  6. filtrationthe precpitate is collected by filtration
  7. customthe insoluble portion is removed by filtration
  8. dry with materialThe filtrate is then dried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-46c6ad2028544841ab0784f4575a9a43
Source dataset
uspto-grants-2002_04
Patent number
US06380187B2

Reaction notes

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