Water → 2-(5-Phenyl-1,3,4-thiadiazol-2-yl)benzoic acid

HRID 268145Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[S:9][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:11][N:12]=1.[Mn]([O-])(=O)(=O)=[O:20].[K+].[Mn]([O-])(=O)(=O)=O.[OH2:30]>>[C:13]1([C:10]2[S:9][C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[C:1]([OH:20])=[O:30])=[N:12][N:11]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Reactant 4

HCID 962Water

HCID 24401Permanganate

HCID 516875Potassium Permanganate

HCID 123920962-(2-Methylphenyl)-5-phenyl-1,3,4-thiadiazole

Product 1

HCID 123920982-(5-Phenyl-1,3,4-thiadiazol-2-yl)benzoic acid

Procedure

2-o-Methylphenyl-5-phenyl-1,3,4-thiadiazole (25 g.) was suspended in a solution of potassium permanganate (40 g.) in water (475 ml.). The reaction mixture was stirred and refluxed until the color of permanganate had discharged, then filtered and cooled. Unreacted 2-o-methylphenyl-5-phenyl-1,3,4-thiadiazole which separated was removed by filtration. When this filtrate was acidified, 2-(5-phenyl-1,3,4-thiadiazol-2-yl)benzoic acid was obtained and recrystallized from ethanol to give white crystals, M.P. 178°-180°. Analysis gave C, 63.37; H, 3.74; N, 9.74. C15H10N2O2S requires C, 63.83; H, 3.51; N, 9.93.

Workup

filtrationfiltered
temperaturecooled
customUnreacted 2-o-methylphenyl-5-phenyl-1,3,4-thiadiazole which separated
customwas removed by filtration

Sources & evidence

ORD record: ord-1c21e804ee4942189ab2f039e687e103
Source dataset: uspto-grants-1976_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03947263

Reaction notes

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