1,1'-Carbonyldiimidazole → HCID 86658578, compound

2-(2-Chloro-4-nitrophenyl)acetic acid (67.2 mmol) was dissolved in DMF (500 mL) to give a colorless solution. CDI (87 mmol) was added in one portion. The mixture was stirred at room temperature until bubbling of the solution ceased. Methoxylamine hydrochloride (87 mmol) was added poroom temperatureion wise, and the resulting mixture was stirred at room temperature over night. The resulting suspension was concentrated under reduced pressure to 100 mL and then diluted with EtOAc (1200 mL). The resulting solution was washed with water (2×700 mL) and the aqueous layer was extracted back with EtOAc (2×600 mL). The organic layers were combined and washed with sat. aq. NaHCO3 (1×1200 mL) and sat. aq. NaCl (1×1200 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to give 2-(2-chloro-4-nitrophenyl)-N-methoxyacetamide as a solid (85%).

1. customto give a colorless solution
2. customuntil bubbling of the solution
3. stirringthe resulting mixture was stirred at room temperature over night
4. concentrationThe resulting suspension was concentrated under reduced pressure to 100 mL
5. additiondiluted with EtOAc (1200 mL)
6. washThe resulting solution was washed with water (2×700 mL)
7. extractionthe aqueous layer was extracted back with EtOAc (2×600 mL)
8. washwashed with sat. aq. NaHCO3 (1×1200 mL) and sat. aq. NaCl (1×1200 mL)
9. dry with materialThe organic layer was dried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure

ORD record

ord-5f19226f23b348f2806e8584e4e82180

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08232283B2