Hydrochloric Acid → HCID 89906601, compound

To a solution of methyl 4-[(E)-(hydroxyimino)methyl]benzoate (6.3 g, 39 mmol) in 2-methyltetrahydrofuran (60 mL) and of dimethyl acetamide (7 mL) was added a solution of HCl in dioxane (4.0 M, 195 uL, 0.78 mmol) and the mixture was cooled in an ice bath. NCS (5.48 g, 41.0 mmol) was added portionwise maintaining the internal temperature below 10 C. The mixture was stirred at 20 C for 30 min and then was cooled in an ice bath. MsCl (4.7 g, 41 mmol) was added followed by DIPEA (5.55 g, 43 mmol) dropwise maintaining the internal temperature below 10 C. The mixture was warmed to 20 C and stirred for 1 h. The reaction was partitioned between EtOAc and water and the organic layer was washed with water (3×), brine (1×), dried over MgSO4 and the solvent removed to give a colorless solid (5.52 g, 54% yld).

1. temperaturethe mixture was cooled in an ice bath
2. temperaturemaintaining the internal temperature below 10 C
3. temperaturewas cooled in an ice bath
4. temperaturedropwise maintaining the internal temperature below 10 C
5. temperatureThe mixture was warmed to 20 C
6. stirringstirred for 1 h
7. customThe reaction was partitioned between EtOAc and water
8. washthe organic layer was washed with water (3×), brine (1×)
9. dry with materialdried over MgSO4
10. customthe solvent removed
11. customto give a colorless solid (5.52 g, 54% yld)

ORD record

ord-67640bb963dc4ff38a00a70cafdd03ed

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296735B2