Chloroacetyl chloride → HCID 10964875, compound

Temperature

-70 °C

To a mixture of 2-amino-1-butanol (5.0 mL, 53 mmol) and triethyl amine (15.0 mL, 111 mmol) in dichloromethane (20 mL) at -70° C. was added chloroacetyl chloride (4.6 mL, 58 mmol) dropwise. The reaction mixture was stirred at -70° C. for 15 min. and then was allowed to warm to rt. It was diluted with EtOAc (50 mL) and the reaction was quenched by adding water (50 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (3×30 mL). The combined organic layers was concentrated to afford 2-(2-chloroacetamido)-1-butanol (8.6 g, 98%) as a brown solid. 1H NMR (CDCl3) δ6.75 (bs, 1 H), 4.10 (s, 2 H), 4.08 (dd, 1 H), 3.90 (m, 1 H), 3.68 (m, 2 H), 2.98 (bs, 1 H), 1.60 (m, 2 H), 0.97 (t, 3 H).

1. temperatureto warm to rt
2. customthe reaction was quenched
3. additionby adding water (50 mL)
4. customThe organic layer was separated
5. extractionthe aqueous layer was extracted with EtOAc (3×30 mL)
6. concentrationThe combined organic layers was concentrated

ORD record

ord-77f3ddc082c04c4d9b9ec77d10a3b7b3

Source dataset

uspto-grants-2000_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06040321