Sodium Hydroxide → beta-Amino-4'-[(difluoromethyl)thio][1,1'-biphenyl]-4-ethanol
Reaction equation
[F:1][CH:2]([F:28])[S:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]([NH:19]C(=O)C3C=CC=CC=3)[CH2:17][OH:18])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.[OH-].[Na+]>C(O)C>[NH2:19][CH:16]([C:13]1[CH:14]=[CH:15][C:10]([C:7]2[CH:8]=[CH:9][C:4]([S:3][CH:2]([F:28])[F:1])=[CH:5][CH:6]=2)=[CH:11][CH:12]=1)[CH2:17][OH:18]Participants
Procedure
A mixture of 5.14 g of N-[1-[4'-[(difluoromethyl)thio][1,1'-biphenyl]-4-yl]-2-hydroxyethyl]benzamide, 9.5 mL of sodium hydroxide solution (1.54 g, 38.5 mmol in 9.5 mL water), and 36 mL of ethanol was boiled for ~40 h. The mixture was allowed to cool to room temperature and the solvent was removed under reduced pressure. The residue was dissolved in water, and the aqueous mixture was extracted with 3×70 mL of ethyl acetate. The combined extracts were dried and the solvent was removed under reduced pressure. The white solid obtained was washed with a little ether to give the product 2.69 g (70% yield); m.p. 107.5-110.5° C. IR(Nujol): 3333, 3281, 1597 1313, 1073, 1042, 895, 820 cm-1. 1H-NMR(CDCl3): δ3.56-3.63 (m, 1H), 3.76-3.81 (m, 1H), 4.09-4.13 (m, 1H), 6.86 (t, J=57.0 Hz, 1H), 7.41-7.65 (m, 8H).
Workup
- waitwas boiled for ~40 h
- customthe solvent was removed under reduced pressure
- dissolutionThe residue was dissolved in water
- extractionthe aqueous mixture was extracted with 3×70 mL of ethyl acetate
- customThe combined extracts were dried
- customthe solvent was removed under reduced pressure
- customThe white solid obtained
- washwas washed with a little ether
Sources & evidence
- ORD record
- ord-7507f7092f7843bcae22cf79a628d789
- Source dataset
- uspto-grants-2000_05
- Patent number
- US06063932
Reaction notes
Loading…