Diethyl Ether → 2-(3-Chloro-2-methylsulphenylphenyl)-4,4-dimethyloxazoline

HRID 342979Notes

Reaction equation

HRID 342979 reaction equation
C([Li])CCC.[Cl:6][C:7]1[CH:8]=[C:9]([C:13]2[O:14][CH2:15][C:16]([CH3:19])([CH3:18])[N:17]=2)[CH:10]=[CH:11][CH:12]=1.[CH3:20][S:21]SC.CCOCC>C1COCC1>[Cl:6][C:7]1[C:8]([S:21][CH3:20])=[C:9]([C:13]2[O:14][CH2:15][C:16]([CH3:19])([CH3:18])[N:17]=2)[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 12232Dimethyl DisulfideHCID 10798476Oxazole, 2-(3-chlorophenyl)-4,5-dihydro-4,4-dimethyl-HCID 178418339Butyllithium

Product 1

HCID 544052592-(3-Chloro-2-methylsulphenylphenyl)-4,4-dimethyloxazolineYield 96.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-65 °C

Procedure

n-Butyllithium (2.5M in hexane, 4.2 ml) was added to a solution of 2-(3-chlorophenyl)-4,4-dimethyloxazoline (2 g) in THF while maintaining the temperature below -45° C. The mixture was stirred at -65° C. for 3 hours. Dimethyl disulphide (1.0 g) was added and the mixture was stirred at -65° C. for 2.5 hours and allowed to warm to room temperature. Ether was added and the mixture was washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give 2-(3-chloro-2-methylsulphenylphenyl)-4,4-dimethyloxazoline (2.35 g) as a yellow oil NMR (CDCl3) 2.0(s,6H) 3.0(s,3H) 4.65(s,2H) 7.5-8.1(m,3H).

Workup

  1. temperaturewhile maintaining the temperature below -45° C
  2. stirringthe mixture was stirred at -65° C. for 2.5 hours
  3. temperatureto warm to room temperature
  4. washthe mixture was washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-51803de05b404ec397fca9746d747480
Source dataset
uspto-grants-1999_01
Patent number
US05859283

Reaction notes

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