Tetrahydrofuran → 4-(4-Chloromethylphenoxymethyl)-5-methyl-2-phenylthiazole

HRID 1294125Notes

Reaction equation

HRID 1294125 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21]O)=[CH:17][CH:16]=1.O1CCCC1.S(Cl)([Cl:30])=O>C1(C)C=CC=CC=1>[Cl:30][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[S:6][C:2]=2[CH3:1])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 688862694-(5-Methyl-2-phenyl-4-thiazolylmethoxy)benzyl alcohol

Product 1

HCID 178613534-(4-Chloromethylphenoxymethyl)-5-methyl-2-phenylthiazoleYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a mixture of [4-[(5-methyl-2-phenyl-4-thiazolyl)methoxy]phenyl]methanol (4.50 g), tetrahydrofuran (50 mL) and toluene (50 mL) was added a solution (5 mL) of thionyl chloride (1.5 mL) in toluene under ice-cooling, and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was concentrated and the residue was dissolved in ethyl acetate. The mixture was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give colorless crystals (4.50 g, 94%) of 4-(4-chloromethylphenoxymethyl)-5-methyl-2-phenylthiazole. melting point: 100-101° C.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe mixture was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8625930261c1478fb2dabbb43d0ed008
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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