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

HRID 2256920Notes

Reaction equation

HRID 2256920 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-6bc1d478be9a441d8ae86431ec8f9acb
Source dataset
uspto-grants-1997_08
Patent number
US05656573

Reaction notes

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