HCID 178418443, compound → HCID 178448975, compound

This compound was prepared using methodology described in Synthesis 1999, 2138-2144. To a solution of 21.2 g (99.2 mmol) butyl-[1-(2-chloro-6-fluoro-phenyl)-meth-(E)-ylidene]-amine in 150 ml tetrahydrofuran at 0° C. was added dropwise 38.0 ml (114 mmol) of a 3 M solution of ethylmagnesium bromide in ether at such a rate that the temperature of the reaction mixture was maintained below 20° C. After the addition was complete, the reaction mixture was stirred for a further 1 h at room temperature. The reaction mixture was then quenched by dropwise addition of water and diluted with ethyl acetate. The mixture was washed sequentially with water and with saturated brine, then the organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The residue was resuspended in carbon tetrachloride and concentrated in vacuo again to afford 19.7 g (89%) of the title compound as a yellow oil which was used in the next step without further purification. MS (ISP): 226.3 ([{37Cl}M+H]+), 224.3 ([{35Cl}M+H]+). 1H NMR and MS analysis indicated that this material contained ca 13% of the by-product butyl-[1-(2-ethyl-6-fluoro-phenyl)-meth-(E)-ylidene]-amine. MS (ISP): 208.3 ([M+H]+).

1. customThis compound was prepared
2. customdescribed in Synthesis 1999, 2138-2144
3. temperaturewas maintained below 20° C
4. additionAfter the addition
5. customThe reaction mixture was then quenched by dropwise addition of water
6. additiondiluted with ethyl acetate
7. washThe mixture was washed sequentially with water and with saturated brine
8. dry with materialthe organic phase was dried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. concentrationconcentrated in vacuo again

ORD record

ord-2b0deb6f528b4e28bf5d3fbd6d754814

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158668B2