Water → 4-[4'-[(Difluoromethyl)thio][1,1'-biphenyl]-4-yl]-2-(2,6-difluorophenyl)-4,5-dihydrooxazole

HRID 1108156Notes

Reaction equation

HRID 1108156 reaction equation
[OH-].[Na+].Cl[CH2:4][CH:5]([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:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([S:18][CH:19]([F:21])[F:20])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.O>CN(C=O)C>[F:20][CH:19]([F:21])[S:18][C:15]1[CH:16]=[CH:17][C:12]([C:9]2[CH:10]=[CH:11][C:6]([CH:5]3[CH2:4][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:7][CH:8]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 18786412N-[2-chloro-1-[4'-[(difluoromethyl)thio][1,1'-biphenyl]-4-yl]ethyl]-2,6-difluorobenzamide

Product 1

HCID 154525844-[4'-[(Difluoromethyl)thio][1,1'-biphenyl]-4-yl]-2-(2,6-difluorophenyl)-4,5-dihydrooxazoleYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A portion of 0.093 g (1.16 mmol) of sodium hydroxide solution (50%) was added dropwise to 0.53 g (1.16 mmol) of N-[2-chloro-1-[4'-[(difluoromethyl)thio][1,1'-biphenyl]-4-yl]ethyl]-2,6-difluorobenzamide in 3.5 mL of DMF. After 3 h, a further portion, 0.045 g (0.56 mmol) of sodium hydroxide solution (50%) was added. When the reaction was completed by TLC, the mixture was poured into water (50 mL). The aqueous mixture was extracted with 3×50 mL of ethyl acetate. The combined extracts were dried and the solvent was removed under reduced pressure. The residue was dissolved in 100 mL of ether. The ethereal solution was washed with 50 mL of water, dried, and the solvent was removed under reduced pressure gave the product, 0.35 g (72% yield), as a pale yellow solid, indistinguishable from the product of Example 6.

Workup

  1. extractionThe aqueous mixture was extracted with 3×50 mL of ethyl acetate
  2. customThe combined extracts were dried
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in 100 mL of ether
  5. washThe ethereal solution was washed with 50 mL of water
  6. customdried
  7. customthe solvent was removed under reduced pressure
  8. customgave the product, 0.35 g (72% yield)

Sources & evidence

ORD record
ord-b953b0a51a124c79b3db01f711257b12
Source dataset
uspto-grants-2000_05
Patent number
US06063932

Reaction notes

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