3-Chlorobenzoic Acid → 5-(3-Chlorophenyl)-N-methyl-1,3,4-thiadiazol-2-amine

HRID 2418941Notes

Reaction equation

HRID 2418941 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=O.[CH3:11][NH:12][C:13](=[S:16])[NH:14][NH2:15].P(Cl)(Cl)(Cl)=O>O1CCOCC1>[CH3:11][NH:12][C:13]1[S:16][C:5]([C:4]2[CH:8]=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=2)=[N:15][N:14]=1

Participants

5

Reactant 3

HCID 4473-Chlorobenzoic AcidHCID 24813Phosphorus oxychlorideHCID 2723853N-Methylhydrazinecarbothioamide

Product 1

HCID 152779685-(3-Chlorophenyl)-N-methyl-1,3,4-thiadiazol-2-amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A well-stirred mixture of 125 g (0.8 mole) of 3-chlorobenzoic acid and 84 g (0.8 mole) of 4-methylthiosemicarbazide in 700 ml of dioxane was heated until the solution was homogeneous. Phosphorus oxychloride (123 g, 0.8 mole) was added dropwise to the resulting solution at a rate to maintain the dioxane at gentle reflux.

Workup

  1. temperaturewas heated until the solution

Sources & evidence

ORD record
ord-e901257d757f4fa482a523ba7025f3ba
Source dataset
uspto-grants-1978_08
Patent number
US04104053

Reaction notes

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