Triethylamine → 2,2,2-trifluoro-N'-(4-methoxyphenyl)ethanehydrazonamide

To a solution of trifluoroacetoamidine (4.24 g, 37.8 mmol) in methanol (20 mL), were added 4-methoxyphenylhydrazine hydrochloride (4.72 g, 27 mmol) and then triethylamine (3.77 mL, 27 mmol) at room temperature. The mixture was stirred for 6 hours. The solvent was removed under reduced pressure. 20 mL of water and 50 mL of ethyl acetate-tetrahydrofuran (9:1) were added to the residue and the organic layer was separated and the aqueous layer was extracted with 50 mL of ethyl acetate-tetrahydrofuran (9:1). A combined organic layer was washed with water and brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure to give 2,2,2-trifluoro-N′-(4-methoxyphenyl)ethanehydrazonamide (6.82 g, 108.2% yield). The residue was used for the next reaction without purification.

1. customat room temperature
2. customThe solvent was removed under reduced pressure
3. addition20 mL of water and 50 mL of ethyl acetate-tetrahydrofuran (9:1) were added to the residue
4. customthe organic layer was separated
5. extractionthe aqueous layer was extracted with 50 mL of ethyl acetate-tetrahydrofuran (9:1)
6. washA combined organic layer was washed with water and brine
7. dry with materialdried over magnesium sulfate
8. customThe solvent was removed under reduced pressure

ORD record

ord-46f0bbabc90a4230b8163427f08345aa

Source dataset

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06927230B2