Hydrochloric Acid → HCID 19102214, compound

HRID 1974769Notes

Reaction equation

HRID 1974769 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C([Li])CCC.F[C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[C:22]1[O:23][CH2:24][C:25]([CH3:28])([CH3:27])[N:26]=1.Cl>C1COCC1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:17]2[CH:18]=[C:19]([F:21])[CH:20]=[CH:15][C:16]=2[C:22]2[O:23][CH2:24][C:25]([CH3:28])([CH3:27])[N:26]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 677894-FluorothiophenolHCID 19102230HCID 19102230, compoundHCID 178418339Butyllithium

Product 1

HCID 19102214HCID 19102214, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To 4-fluorothiophenol (9.26 g; 72.2 mmol.) in dry THF under nitrogen and cooled to -78° C. was added n-butyllithium (45.2 ml of 1.6M) dropwise affording a white slurry. To this mixture was added 2-(2,4-difluorophenyl)-4,4-dimethyloxazoline (7.63 g; 36.1 mmol.) in 20 ml of dry THF dropwise. The reaction mixture was allowed to warm to room temperature overnight. An additional 50 ml of THF was added to afford a solution and the reaction stirred over the weekend. The mixture was poured into water, acidified to pH 5 with 1N HCl. The mixture was extracted twice with diethyl ether and the organics combined, washed with water and then 0.2N NaOH. The organic layer was washed again with water and then brine, dried over MgSO4, and concentrated to afford 13.2 g of crude product which after recrystallization from hexane afforded 8.82 g of the subtitle compound.

Workup

  1. customdropwise affording a white slurry
  2. customto afford a solution
  3. extractionThe mixture was extracted twice with diethyl ether
  4. washwashed with water
  5. washThe organic layer was washed again with water
  6. dry with materialbrine, dried over MgSO4
  7. concentrationconcentrated
  8. customto afford 13.2 g of crude product which
  9. customafter recrystallization from hexane

Sources & evidence

ORD record
ord-46a40075a9ff44e1854a7c09edd86bbd
Source dataset
uspto-grants-1994_02
Patent number
US05283361

Reaction notes

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