Sodium Hydroxide → HCID 11004848, compound

HRID 1108167Notes

Reaction equation

HRID 1108167 reaction equation
Cl[CH2:2][CH:3]([NH:22][C:23](=[O:32])[C:24]1[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:25]=1[F:31])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH:19]([F:21])[F:20])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.[OH-].[Na+]>C(O)(C)C.O>[F:20][CH:19]([F:21])[S:16]([C:13]1[CH:14]=[CH:15][C:10]([C:7]2[CH:8]=[CH:9][C:4]([CH:3]3[CH2:2][O:32][C:23]([C:24]4[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:25]=4[F:31])=[N:22]3)=[CH:5][CH:6]=2)=[CH:11][CH:12]=1)(=[O:18])=[O:17]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11049198HCID 11049198, compound

Product 1

HCID 11004848HCID 11004848, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

To a slurry of 9.18 g (18.9 mmol) of N-[2-chloro-1-[4'-[(difluoromethyl) -sulfonyl][1,1'-biphenyl]-4-yl]ethyl]-2,6-difluorobenzamide in 70 mL of isopropanol was added a solution of 1.8 g (22.5 mmol) of aqueous 50% NaOH at 25-30° C. The mixture was allowed to stir for 30 minutes at ambient temperature, diluted with 40 mL of water, and filtered. The solid product was washed with 20 mL of 50% aqueous isopropanol and suction-dried to afford 7.5 g (88%) of 4-[4'-[(difluoromethyl)sulfonyl][1,1'-biphenyl]-4-yl]-2-(2,6-difluorophenyl)-4,5-dihydrooxazole, m.p. 107-111° C. An analytical sample was prepared by recrystallization from isopropanol, m.p. 109-111° C. IR(KBr): 1669, 1622, 1593, 1485, 1469, 1395, 1345, 1300, 1285, 1240, 1168, 1161, 1114, 1081, 1053, 1041, 1012, 822, 793 cm-1. UV(CH2Cl2): λmax =279 nm (ε=25.9×103). 1H-NMR (benzene-d6): δ3.9 (t, 1H), 4.25 (dd, 1H), 5.15 (dd, 1H), (dq, 2H), 5.68 (m, 1H), 6.22 (t, 1H, J=53 Hz), 6.7 (br d, 1H), 7.0 (t, 2H, J=9 Hz), 7.41 (m, 1H), 7.53 (d, 2H), 7.65 (d, 2H), 7.83 (d, 2H), 8.05 (d, 2H). 13C-NMR (CDCl3): δ69.9, 74.6, 107.1 (dd, JCF =2, 23 Hz), 114.8, 127.6, 127.9, 128.1, 131.2, 132.2. 19F-NMR (CDCl3): δ-112.1 (t, JHF =7.3 Hz), -121.8 (d, JHF =53 Hz).

Workup

  1. filtrationfiltered
  2. washThe solid product was washed with 20 mL of 50% aqueous isopropanol
  3. customsuction-dried

Sources & evidence

ORD record
ord-e5ee29f025244a71a5c677c21be503c2
Source dataset
uspto-grants-2000_05
Patent number
US06063932

Reaction notes

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