Chloroacetyl chloride → HCID 59817752, compound

Temperature

60 °C

At 0° C., a solution of 2-amino-4-nitrophenol (6.24 g, 40.5 mmol) in DMF (62 mL) is treated with K2CO3 (8.44 g, 61.1 mmol) and chloroacetyl chloride (X. Huang, C. Chan, Synthesis 1984, 31, 851.) (3.5 mL, 44.0 mmol), stirred at the same temperature for 40 min, warmed to 60° C., and stirred for 23 h, cooled to 0° C., and treated with KI (1.32 g, 7.95 mmol) and a solution of 1-methoxy-3-(p-toluenesulfonyloxy)propane (12.1 g, 49.5 mmol) in DMF (24 mL). After adding 60% of NaH (2.00 g, 50.0 mmol) over 10 min, the mixture is stirred at 0° C. for 1 h, warmed to 60° C., stirred for 24 h, and treated with H2O (650 mL). After extraction of the mixture with EtOAc (3×80 mL) and Et2O (3×80 mL), the combined org. layer is washed with H2O (2×50 mL), dried (Na2SO4), and evaporated. A SiO2 flash chromatography (300 g, hexane/EtOAc 5:4) gives 4-(3-methoxypropyl)-6-nitro-4H-benzo[1,4]oxazin-3-one as yellow solid.

1. stirringstirred for 23 h
2. temperaturecooled to 0° C.
3. additiontreated with KI (1.32 g, 7.95 mmol)
4. stirringthe mixture is stirred at 0° C. for 1 h
5. temperaturewarmed to 60° C.
6. stirringstirred for 24 h
7. extractionAfter extraction of the mixture with EtOAc (3×80 mL) and Et2O (3×80 mL)
8. washlayer is washed with H2O (2×50 mL)
9. dry with materialdried (Na2SO4)
10. customevaporated

ORD record

ord-2b26609f207d4903903a136896d402cf

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129411B2