Nitric Acid → Ethyl 2-iodo-4-(trifluoromethyl)-5-thiazolecarboxylate

HRID 279747

Reaktionsgleichung

Reaktionsgleichung von HRID 279747
N[C:2]1[S:3][C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.P(=O)(O)(O)O.[N+]([O-])(O)=O.N([O-])=O.[Na+].[I-:29].[K+]>O>[I:29][C:2]1[S:3][C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1

Komponenten

7

Edukt 5

HCID 944Nitric AcidHCID 1004Phosphoric AcidHCID 4875Potassium IodideHCID 676565-Thiazolecarboxylic acid, 2-amino-4-(trifluoromethyl)-, ethyl esterHCID 23668193Sodium Nitrite

Produkt 1

HCID 13593392Ethyl 2-iodo-4-(trifluoromethyl)-5-thiazolecarboxylateAusbeute 25,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a cold (-5° C.) solution of 4.0 g (0.0166 mole) of ethyl 2-amino-4trifluoromethyl-5-thiazolecarboxylate, prepared according to U.S. Pat. No. 2,726,237, in 30 ml. of 85% phosphoric acid and 30 ml. of 70% nitric acid was added a solution of 1.26 g (0.0166 mole) of sodium nitrite in 10 ml. of water in 10 minutes. The reaction mixture was stirred for 10 minutes and poured into a solution of 10 g of potassium iodide in 100 ml. of water. The reaction mixture was stirred overnight and extracted with ether. The ether solution was dried and concentrated and the residue was chromatographed on silica gel to give 1.5 g of the desired product, m.p. 75°-76° C.

Aufarbeitung

  1. stirringThe reaction mixture was stirred overnight
  2. extractionextracted with ether
  3. dry with materialThe ether solution was dried
  4. concentrationconcentrated
  5. customthe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-86f4d5e582f24b94b6709ab592ac9bf3
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04586948

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