Triethylamine → Ethyl 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(cyclopropyloxyimino)acetate

HRID 1074342Notes

Reaction equation

Cl.[C:2]([C:5](=[N:11][O:12][CH:13]1[CH2:15][CH2:14]1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[NH:4])[NH2:3].C(N(CC)CC)C.BrBr.[S-:25][C:26]#[N:27].[K+]>CO.C(OCC)(=O)C>[NH2:27][C:26]1[S:25][N:3]=[C:2]([C:5](=[N:11][O:12][CH:13]2[CH2:14][CH2:15]2)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[N:4]=1

Participants

Conditions

Temperature: -5 °C

Procedure

To a solution of ethyl 2-amidino-2-(cyclopropoxyimino)acetate hydrochloride (syn isomer) (1.44 g) in methanol (11 ml) was added triethylamine (3.06 ml) at -15° C. To the solution was dropwise added bromine (852 mg) at -5° C. After the solution was stirred at -5° C. for 2 minutes, to the solution was added a solution of potassium thiocyanate (518 mg) in methanol (5 ml) at -5° C. The mixture was allowed to be stirred under ice-cooling for 2 hours. The mixture was concentrated in vacuo to give a residue. The residue was dissolved in ethyl acetate. The solution was washed successively with 1N hydrochloric acid, saturated aqueous solution of sodium bicarbonate, and saturated aqueous solution of sodium chloride, dried over magnesium sulfate, concentrated in vacuo, and triturated with diethyl ether to give ethyl 2-(5-amino-l,2,4-thiadiazol3-yl)-2-(cyclopropyloxyimino)acetate (syn isomer)(769 mg) as a crystal.

Workup

customat -5° C
stirringto be stirred under ice-
temperaturecooling for 2 hours
concentrationThe mixture was concentrated in vacuo
customto give a residue
washThe solution was washed successively with 1N hydrochloric acid, saturated aqueous solution of sodium bicarbonate, and saturated aqueous solution of sodium chloride
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
customtriturated with diethyl ether

Sources & evidence

ORD record: ord-aca11c7722844dd38692216ba881e37e
Source dataset: uspto-grants-1990_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04973699

Reaction notes

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