Sulfuric Acid → 2-(Trichloromethyl)-1,3,4-thiadiazole

Reaction equation

[Cl:1][C:2]([Cl:13])([Cl:12])[C:3]1[S:4][C:5](C(Cl)(Cl)Cl)=[N:6][N:7]=1.S(=O)(=O)(O)O>>[Cl:1][C:2]([Cl:13])([Cl:12])[C:3]1[S:4][CH:5]=[N:6][N:7]=1

Participants

Reactant 2

HCID 1118Sulfuric Acid

HCID 126396672,5-Bis(trichloromethyl)-1,3,4-thiadiazole

Product 1

HCID 126397022-(Trichloromethyl)-1,3,4-thiadiazoleYield 83%

Procedure

6.4 parts by weight of 2,5-bis-trichloromethyl-1,3,4-thiadiazole is heated in 30 parts by volume of 91% sulfuric acid for 6 minutes at 175° to 185° C. The reaction mixture is subsequently poured carefully on to ice and the precipitated solid is filtered off. The reaction product is washed with water and treated with 20 parts by volume of methanol, and the minor amounts of undissolved starting material are filtered off. Concentration of the methanolic solution gives 3.4 parts (83% of theory) of 2-trichloromethyl-1,3,4-thiadiazole having a melting point of 58° C.

Workup

additionThe reaction mixture is subsequently poured carefully on to ice
filtrationthe precipitated solid is filtered off
washThe reaction product is washed with water
additiontreated with 20 parts by volume of methanol
filtrationare filtered off

Sources & evidence

ORD record: ord-797aee6e2b724ad3b0b420e404547833
Source dataset: uspto-grants-1978_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04066775

Reaction notes

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