3-Aminobenzonitrile → 5-(3-Aminophenyl)-1,3,4-thiadiazol-2-amine

HRID 1715238Notes

Reaction equation

HRID 1715238 reaction equation
[NH2:1][NH:2][C:3]([NH2:5])=[S:4].[NH2:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[C:10]#N.C([O-])(O)=O.[Na+]>C(O)(C(F)(F)F)=O>[NH2:6][C:7]1[CH:8]=[C:9]([C:10]2[S:4][C:3]([NH2:5])=[N:2][N:1]=2)[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 167023-AminobenzonitrileHCID 516892Sodium BicarbonateHCID 2723789Thiosemicarbazide

Product 1

HCID 594655465-(3-Aminophenyl)-1,3,4-thiadiazol-2-amine

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Thiosemicarbazide (455.7 mg; 5 mmol; 1 eq.) and 3-aminobenzonitrile (Aldrich)(590.7 mg; 5 mmol; 1 eq.) are heated in TFA (2.50 ml) at 60° C. for 4 hours. The mixture becomes a thick yellowish solution. The reaction mixture is poured into ice-water (15 ml) and neutralized with saturated NaHCO3 aqueous solution. The resulting precipitate is filtered, affording 5-(3-aminophenyl)-1,3,4-thiadiazol-2-amine, Amine 2, as white-off solid (291 mg; 30%).

Workup

  1. filtrationThe resulting precipitate is filtered

Sources & evidence

ORD record
ord-4c0069de2ac84c1fbfdfb3ebd534830f
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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