Hydrochloric Acid → 4-(Chloromethyl)-N-hydroxybenzimidoyl chloride

4-(chloromethyl)benzaldehyde oxime 5 (15.8 g, 93.16 mmol) was dissolved in DMF (300 mL). NCS (13.69 g, 102.5 mmol) was added in portions and then HCl in dioxane (100 mL of 4 M, 400.0 mmol) was added slowly, cooling the mixture with an ice water bath to moderate the exotherm, keeping below 33° C. The mixture was stirred at room temperature for 1 hour. The solution was then partitioned between EtOAc and water. The combined organic extract was washed with water and brine (5×200 ml), dried over MgSO4 and concentrated under reduced pressure to give a colourless solid (21.65 g, 95%). 1H NMR (400 MHz, CDCl3) d 4.63 (2H, s), 7.45 (2H, d, J=8 Hz), 7.86 (2H, d, J=8 Hz), 8.36 (1H, s).

1. temperaturecooling the mixture with an ice water bath
2. customkeeping below 33° C
3. customThe solution was then partitioned between EtOAc and water
4. extractionThe combined organic extract
5. washwas washed with water and brine (5×200 ml)
6. dry with materialdried over MgSO4
7. concentrationconcentrated under reduced pressure

ORD 기록

ord-63a4a72e9c5c47e09683053e8fb767d4

출처 데이터셋

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08853217B2