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

HRID 1723584Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1723584
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

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 24408BromineHCID 516872Potassium thiocyanateHCID 73867361Ethyl 2-amidino-2-(cyclopropyloxyimino)acetate hydrochloride

Produkt 1

HCID 54418624Ethyl 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(cyclopropyloxyimino)acetateAusbeute 56,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

To a solution of ethyl 2-amidino-2-(cyclopropyloxyimino)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-1,2,4-thiadiazol-3-yl)-2-(cyclopropyloxyimino)acetate (syn isomer)(769 mg) as a crystal.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-1d0b7f1516744315b3a014ae9de3c16f
Quelldatensatz
uspto-grants-1989_08
Patentnummer
US04861769

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