Hydrochloric Acid → N-methoxy-N-methylthiophene-2-carboxamide

To a solution of thiophene-2-carbonyl chloride (100.6 mL, 940 mmol) and N,O-dimethylhydroxylamine hydrochloride (100.9 g, 1.03 mol) in dichloromethane (1 L) at 0° C. was added dropwise triethylamine (262 mL, 1.88 mol). After stirring at room temperature for 3 h, the reaction mixture was poured into a mixture of water (2 L) and concentrated aq. HCl (36%, 80 mL), the layers were separated and the aqueous layer extracted with dichloromethane (2×200 mL). The combined organic layers were washed with water (200 mL), then dried over MgSO4 and concentrated in vacuo to afford N-methoxy-N-methylthiophene-2-carboxamide [153.4 g, yield 95%; HPLC/MS: m/z=172 (M+H); log P(HCOOH)=1.44].

1. customthe layers were separated
2. extractionthe aqueous layer extracted with dichloromethane (2×200 mL)
3. washThe combined organic layers were washed with water (200 mL)
4. dry with materialdried over MgSO4
5. concentrationconcentrated in vacuo

ORD record

ord-ed06902892164ae59f43c90da3120c8a

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08981111B2