Methanol → 2,3,6-Trifluorobenzoic hydrazide

To 2,3,6-trifluorobenzoyl chloride, (29 g, 0.15 mol) in dichloromethane (200 ml) was added methanol (30 ml) dropwise at 5° C. The solution was allowed to warm to room temperature and was stirred under nitrogen for 2 h. The solvent was removed in uacuo and the residual oil was stirred with hydrazine monohydrate (19 ml, 0.40 mol) in ethanol (120 ml) at reflux for 3 h. The solvent was removed in vacuo, and the residue was partitioned between dichloromethane (400 ml) and water (200 ml). The biphasic mixture was filtered to remove insoluble material, then the aqueous layer was washed with dichloromethane (2×300 ml). The combined organic layers were dried over magnesium sulfate, and were concentrated in vacuo to yield 2,3,6-trifluorobenzoic hydrazide as a white solid (6.0 g). Data for the title compound: 1H NMR (400 MHz, CDCl3) δ 4.18 (2H, br s), 6.93 (1H, m), 7.25 (2H, m); MS (ES+) m/e 191 [MH]+.

1. customThe solvent was removed in uacuo
2. temperatureat reflux for 3 h
3. customThe solvent was removed in vacuo
4. customthe residue was partitioned between dichloromethane (400 ml) and water (200 ml)
5. filtrationThe biphasic mixture was filtered
6. customto remove insoluble material
7. washthe aqueous layer was washed with dichloromethane (2×300 ml)
8. dry with materialThe combined organic layers were dried over magnesium sulfate
9. concentrationwere concentrated in vacuo

ORDレコード

ord-3b11514aa9c3450b96d0535131d338b3

出典データセット

uspto-grants-2002_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06476030B1