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

HRID 1108162Notes

Reaction equation

HRID 1108162 reaction equation
[OH-].[Na+].C1(C)C=CC=CC=1.Cl[CH2:11][CH:12]([NH:29][C:30](=[O:39])[C:31]1[C:36]([F:37])=[CH:35][CH:34]=[CH:33][C:32]=1[F:38])[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([S:25][CH:26]([F:28])[F:27])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1.O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)C>[F:27][CH:26]([F:28])[S:25][C:22]1[CH:23]=[CH:24][C:19]([C:16]2[CH:17]=[CH:18][C:13]([CH:12]3[CH2:11][O:39][C:30]([C:31]4[C:36]([F:37])=[CH:35][CH:34]=[CH:33][C:32]=4[F:38])=[N:29]3)=[CH:14][CH:15]=2)=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 14798Sodium HydroxideHCID 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 76.1%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a well-stirred mixture of 0.6 g of 25% aqueous NaOH, 70 mg of tetrabutylammonium bromide (TBAB) and 10 mL of toluene was added 1.0 g of (+/-)-N-[2-chloro -1-[4'-[(difluoromethyl)thio][1,1'-biphenyl]-4-yl]ethyl]-2,6-difluorobenzamide as a solid. After 45 min, 2 mL of water was added along with 10 mL of diethyl ether. The organic phase was washed with water, dried (MgSO4), filtered, and concentrated to dryness. The residue was triturated with hexanes, filtered, and suction-dried to afford 0.70 g of product, m.p. 75-77° C. The 1H-NMR (CDCl3) spectrum was the same as that the product of Example 6.

Workup

  1. washThe organic phase was washed with water
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe residue was triturated with hexanes
  6. filtrationfiltered
  7. customsuction-dried

Sources & evidence

ORD record
ord-66dcbbd48a98494a8a0f06a9c4d70715
Source dataset
uspto-grants-2000_05
Patent number
US06063932

Reaction notes

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