Thionyl Chloride → HCID 23076418, compound

HRID 2221691Notes

Reaction equation

HRID 2221691 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:26]O)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[N:12]=[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)[O:14][C:15]=1[CH3:16].S(Cl)([Cl:30])=O>C1(C)C=CC=CC=1>[Cl:30][CH2:26][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11]2[N:12]=[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=3)[O:14][C:15]=2[CH3:16])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 23076542HCID 23076542, compound

Product 1

HCID 23076418HCID 23076418, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of (3-methoxy-4-{[5-methyl-2-(3-nitrophenyl)-1,3-oxazol-4-yl]methoxy}phenyl)methanol (5.92 g) and toluene (250 ml) was added thionyl chloride (2.19 mL), and the mixture was heated under reflux for 1.5 hrs. The reaction mixture was concentrated and ethyl acetate was added to the residue. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated to give 4-[(4-chloromethyl-2-methoxyphenoxy)methyl]-5-methyl-2-(3-nitrophenyl)-1,3-oxazole (6.31 g, yield 100%) as colorless crystals. Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 166-168° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hrs
  3. concentrationThe reaction mixture was concentrated
  4. additionethyl acetate was added to the residue
  5. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a7674e4d26974673b4a2aa98566c1111
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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