Phenylacetyl chloride → N-octyl-cis-3-(phenylacetylthio)acrylamide

Temperatur

-78 °C

To a cooled (-78° C.), stirred solution of 2.0 g (0.0094 mol) of 2-octyl-4-isothiazolin-3-one in 50 ml of anhydrous tetrahydrofuran under nitrogen was added dropwise 2.82 ml (0.0028 mol) of a 1.0M solution of lithium aluminum hydride in tetrahydrofuran over a 20 min. period. After the addition the mixture was stirred at -78° C. for 1 hr. Over a 15 min period 1.24 ml (0.0094 mol) of phenylacetyl chloride was added. After this addition the mixture was allowed to warm to room temperature. After 12 hr the reaction mixture was a white solid suspended in an orange solution. The mixture was filtered and the filtrate was diluted with ethyl acetate and washed once with aqueous saturated sodium bicarbonate solution. The organic layer was set aside and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed once with water, with brine, and dried over anhydrous magnesium sulfate. Filtration and removal of solvents gave N-octyl-cis-3 -(phenylacetylthio)acrylamide as an oil which crystallized upon standing to give 3.0 g (96% yield) of a white solid whose NMR is reported in Table 2.

1. additionAfter the addition the mixture
2. additionAfter this addition the mixture
3. temperatureto warm to room temperature
4. waitAfter 12 hr the reaction mixture was
5. filtrationThe mixture was filtered
6. additionthe filtrate was diluted with ethyl acetate
7. washwashed once with aqueous saturated sodium bicarbonate solution
8. extractionthe aqueous layer was extracted three times with ethyl acetate
9. washThe combined organic layers were washed once with water, with brine
10. dry with materialdried over anhydrous magnesium sulfate
11. filtrationFiltration and removal of solvents

ORD-Eintrag

ord-6a7c9986b5cd44bd9cbf6d9e2a8af70f

Quelldatensatz

uspto-grants-1992_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05166390