N,N,N',N'-Tetramethylethylenediamine → HCID 18519016, compound

Temperature

0 °C

To 7,8-dihydro-6H-5-oxa-9-thia-benzocycloheptene (16.2 g, 97 mmol) in 250 mL of dry hexane was added tetramethylethylene diamine (16 mL, 106 mmol). The solution was cooled to 0° C. and n-butyllitium (1.6 M solution in hexane, 73 mL, 116.8 mmol) was slowly added with stirring. A tan-colored precipitate slowly started to form and some gas evolution occured. The suspension was stirred at rt for 18 h, after which CO2 gas was bubbled though it for 20 min. An exothermic reaction occured. The mixture was diluted with 300 mL ethyl acetate and 4 N HCl. After all solids dissolved, the organic layer was washed with 1 N HCl. The acid was extracted into 10 tho water layer using sat. NaHCO3. The aqueous layer was washed with ethyl acetate and treated with 10 N HCl to pH 1. Extraction with ethyl acetate (2×250 mL), drying over Na2SO4 and concentration yielded the compound as a tan solid (16.5 g, 81%). MS [M−H]− 209.

1. customto form
2. stirringThe suspension was stirred at rt for 18 h
3. customafter which CO2 gas was bubbled though it for 20 min
4. customAn exothermic reaction
5. dissolutionAfter all solids dissolved
6. washthe organic layer was washed with 1 N HCl
7. extractionThe acid was extracted into 10 tho water layer
8. washThe aqueous layer was washed with ethyl acetate
9. additiontreated with 10 N HCl to pH 1
10. extractionExtraction with ethyl acetate (2×250 mL)
11. dry with materialdrying over Na2SO4 and concentration

ORD record

ord-67adbe5343a046f8976016cc03b99eb8

Source dataset

uspto-grants-2003_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06576766B1