1,2-Dimethoxyethane → 4-(Chloromethyl)-5-methyl-2-(4-methylphenyl)-1,3-oxazole

HRID 1169820Notes

Reaction equation

HRID 1169820 reaction equation
Cl.[CH3:2][C:3]1[N+:4]([O-])=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8].CS([Cl:21])(=O)=O.COCCOC>ClCCl>[Cl:21][CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 31297Methanesulfonyl chlorideHCID 198887574,5-Dimethyl-2-(4-methylphenyl)oxazole N-Oxide Hydrochloride

Product 1

HCID 50764854-(Chloromethyl)-5-methyl-2-(4-methylphenyl)-1,3-oxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
15 °C

Procedure

32.8 g (137 mmol) of 4,5-dimethyl-2-p-tolyloxazole 3-oxide hydrochloride were suspended in 165 ml of dichloromethane. 17.5 g (151 mmol) of methanesulfonyl chloride were added. The reaction was stirred at reflux up to full conversion (HPLC). Subsequently, 200 ml of ethylene glycol dimethyl ether were added, and the dichloromethane was distilled off under reduced pressure. The reaction mixture was cooled to 15° C. and 250 ml of water were added. The mixture was stirred at 15° C. for 1 hour. The precipitated product was isolated by filtration with suction, washed with water and dried at elevated temperature under reduced pressure.

Workup

  1. temperatureat reflux up to full conversion (HPLC)
  2. distillationthe dichloromethane was distilled off under reduced pressure
  3. addition250 ml of water were added
  4. stirringThe mixture was stirred at 15° C. for 1 hour
  5. customThe precipitated product was isolated by filtration with suction
  6. washwashed with water
  7. customdried at elevated temperature under reduced pressure

Sources & evidence

ORD record
ord-7d4e6aab83b147648961913dcdde7476
Source dataset
uspto-grants-2010_11
Patent number
US07825144B2

Reaction notes

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