Phenylhydrazine → 1,2,3-Benzothiadiazole

HRID 463596Notes

Reaction equation

HRID 463596 reaction equation
[NH2:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[S:9](Cl)(Cl)=O.S(=NC1C=CC=CC=1)=O.S(Cl)Cl>C(O)C.C1(C)C=CC=CC=1>[S:9]1[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[N:2]=[N:1]1

Participants

7

Reactant 4

HCID 7516PhenylhydrazineHCID 24386Thionyl ChlorideHCID 25353Sulfur dichlorideHCID 70739Benzenamine, N-sulfinyl-

Product 1

HCID 675051,2,3-Benzothiadiazole

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A dinitrobenzene (I) is reacted with, for example, ammonium chloride and iron or with hydrogen gas and palladium on activated carbon in a solvent such as ethanol or toluene and at elevated temperature to give the corresponding aminoaniline (VII). The aminoaniline (VII) is reacted with, for example, thionyl chloride, N-thionyl aniline or sulfur dichloride in a solvent such as toluene or ethanol and at elevated temperature to yield a benzothiadiazole of formula (A'").

Sources & evidence

ORD record
ord-5c6efc75208d43b2a46b7ee1ae47db56
Source dataset
uspto-grants-1985_10
Patent number
US04544400

Reaction notes

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