Thionyl Chloride → 4-(2-Chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole

HRID 1070081Notes

Reaction equation

HRID 1070081 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][C:6]1[O:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH2:17][O:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21]O>C1(C)C=CC=CC=1>[Cl:3][CH2:21][C:20]1[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=1[O:18][CH2:17][C:7]1[N:8]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:10][C:6]=1[CH3:5]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 10957398HCID 10957398, compound

Product 1

HCID 110990364-(2-Chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thionyl chloride (1.69 g) was added dropwise to a stirred suspension of 2-(5-methyl-2-phenyl4-oxazolylmethoxy)benzyl alcohol (4.00 g) in toluene (60 ml) at 0° C. After stirring at room temperature for 2 hours, the reaction mixture was concentrated. The residual crystals were dissolved in ethyl acetate and washed with aqueous sodium bicarbonate and water. The ethyl acetate layer was separated, dried (MgSO4), and concentrated to give 4-(2-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole as crystals. Recrystallization from ethyl acetate-hexane gave colorless needles (3.50 g, yield 82%). m.p. 103-104° C.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. dissolutionThe residual crystals were dissolved in ethyl acetate
  3. washwashed with aqueous sodium bicarbonate and water
  4. customThe ethyl acetate layer was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9d57748de5244c76a535a9a1be5cb7bc
Source dataset
uspto-grants-2001_06
Patent number
US06251926B1

Reaction notes

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