Ammonium Chloride → HCID 19819833, compound

Temperature

0 °C

To a stirred solution of 50 g (0.40 mol) of 3-methyl-2-thiophenecarboxaldehyde in 150 ml of dry tetrahydrofuran at 0° C. was added dropwise 476 ml (0.47 mol) of a 1M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran over a 2 hour period. After stirring the mixture an additional 20 minutes at 0° C., 476 ml (0.47 mol) of a 1M solution of benzyl magnesium chloride in diethyl ether was added dropwise over a 2 hour period. The resulting mixture was allowed to warm to ambient temperature, stirred for 0.5 h longer, and poured into 2.5 L of saturated aqueous ammonium chloride. The mixture was extracted with chloroform (3×500 ml), organic layers combined, dried over MgSO4, and concentrated to dryness giving 85 g of the title amine as an oil. A sample of the product (4 g) was dissolved in isopropanol, made acidic with hydrogen chloride in isopropanol, decolorized with carbon, and reconcentrated to near dryness. The crude hydrochloride salt was recrystallized from a solvent mixture of ethyl acetate and methanol to give 2.5 g of white solid (mp 184°-186° C.).

1. temperatureto warm to ambient temperature
2. stirringstirred for 0.5 h longer
3. extractionThe mixture was extracted with chloroform (3×500 ml), organic layers
4. dry with materialdried over MgSO4
5. concentrationconcentrated to dryness

ORD record

ord-1dd76c4f9667436da9fe946a0dd24ae8

Source dataset

uspto-grants-1992_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05109017