Water → HCID 18348181, Verbindung

Under a nitrogen atmosphere, a stirred solution of 5.0 grams (0.031 mole) 4-(4-methylphenyl)-1,2,3,5-(1H)-tetrazole and 4.8 grams (0.035 mole) of potassium carbonate in 150 mL of acetonitrile was heated to reflux and then cooled to ambient temperature. To this was slowly added 10.0 grams (0.078 mole) of 1-bromo-2-fluoroethane. Upon completion of the addition the reaction mixture was placed in a water bath and cooled to 0° C., where it stirred for one hour. After this time the reaction mixture was heated to reflux, where it stirred for three hours, and then cooled to 0° C., where it stirred for about 18 hours. At the conclusion of this period the reaction mixture was poured into 50 mL of water. The resulting solution was extracted with three 50 mL portions of ethyl acetate. The combined extracts were concentrated under reduced pressure to a residue, which was subjected to column chromatography on silica gel. Elution was accomplished with methylene chloride and acetone. The product-containing fractions were combined and concentrated under reduced pressure, yielding 2.8 grams 1-(2-fluoroethyl)-(4-methylphenyl)-1,2,3,5-(1H)-tetrazole. The NMR spectrum was consistent with the proposed structure.

1. temperatureto reflux
2. additionUpon completion of the addition the reaction mixture
3. customwas placed in a water bath
4. temperaturecooled to 0° C.
5. temperatureAfter this time the reaction mixture was heated
6. temperatureto reflux
7. stirringwhere it stirred for three hours
8. temperaturecooled to 0° C.
9. stirringwhere it stirred for about 18 hours
10. extractionThe resulting solution was extracted with three 50 mL portions of ethyl acetate
11. concentrationThe combined extracts were concentrated under reduced pressure to a residue, which
12. washElution
13. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-9ec13a3d4ad3458d996cabd1ea83c885

Quelldatensatz

uspto-grants-2001_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

USH0002007H1