Bromine → Methyl 5-amino-1,2,4-thiadiazole-3-carboxylate

HRID 543827Notes

Reaction equation

Br.[CH2:2]([O:4][C:5]([C:7]([NH2:9])=[NH:8])=[O:6])C.[Na].BrBr.[S-:13][C:14]#[N:15].[K+]>CO>[NH2:15][C:14]1[S:13][N:9]=[C:7]([C:5]([O:4][CH3:2])=[O:6])[N:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-ethoxycarbonylformamidine. hydrobromide (16.6 g) in absolute methanol (84 ml) was added a solution of sodium (1.93 g) in absolute methanol (42 ml) at 0° C. To the mixture were added alternately bromine (12.8 g) and a solution of sodium (1.93 g) in absolute methanol (42 ml) at 0° C. and then to the suspension was added potassium thiocyanate (8.1 g) in absolute methanol (100 ml). The reaction mixture was stirred for an hour at 0° C. and for an additional 6 hours at ambient temperature. The mixture was filtered through cellulose powder and the filtrate was evaporated to dryness. The residue was dissolved in a mixture of ethyl acetate and water, and then the ethyl acetate layer was separated and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was triturated with diethyl ether to give the title compound (9.0 g), mp. 202° to 205° C.

Workup

filtrationThe mixture was filtered through cellulose powder
customthe filtrate was evaporated to dryness
dissolutionThe residue was dissolved in a mixture of ethyl acetate and water
customthe ethyl acetate layer was separated
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated
customthe residue was triturated with diethyl ether

Sources & evidence

ORD record: ord-f19dbf6ddf3c47fe9e213240f9191c53
Source dataset: uspto-grants-1984_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04447429

Reaction notes

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