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

HRID 2405124Notes

Reaction equation

HRID 2405124 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 (455.69 mg; 5.00 mmol; 1.00 eq.) and 3-aminobenzonitrile (590.69 mg; 5.00 mmol; 1.00 eq.) are heated in TFA (2.50 ml) at 60° C. for 4 h00. The mixture become 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 as white-off solid (291.00 mg; 30.27%).

Workup

  1. filtrationThe resulting precipitate is filtered

Sources & evidence

ORD record
ord-b2be0e7c362249daa0e1ee84bd3541e7
Source dataset
uspto-grants-2014_08
Patent number
US08802861B2

Reaction notes

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