Water → 1-Isothiocyanato-2-(2-methoxyethoxyl)ethane

To a solution of 2-(2-methoxyethoxyl)ethanamine (0.820 g, 6.88 mmol) in DMF (69 mL) at 0° C. was added dropwise a solution of 1,1′-thiocarbonyldiimidazole (1.349 g, 7.57 mmol) in 21 mL of DMF. The mixture was warmed to RT and stirred for 90 min. The mixture was poured into water (130 mL) and extracted with Et2O (70 mL). The Et2O layer was washed with water, dried over Na2SO4, and filtered. The filtrate was concentrated in vacuo (325 torr, bath temp: 24° C.) to afford 1-isothiocyanato-2-(2-methoxyethoxyl)ethane (0.678 g, 4.21 mmol, 61% yield) as a yellow oil. The crude material was used in next step.

1. extractionextracted with Et2O (70 mL)
2. washThe Et2O layer was washed with water
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. concentrationThe filtrate was concentrated in vacuo (325 torr, bath temp: 24° C.)

ORD record

ord-b67a0272595a47ff8821def90437bce1

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394297B2