Tetrahydrofuran → 4-(4-Chloromethylphenoxy)methyl-2-phenylthiazole

HRID 350008Notes

Reaction equation

HRID 350008 reaction equation
S(Cl)([Cl:3])=O.[C:5]1([C:11]2[S:12][CH:13]=[C:14]([CH2:16][O:17][C:18]3[CH:25]=[CH:24][C:21]([CH2:22]O)=[CH:20][CH:19]=3)[N:15]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O1CCCC1>C1(C)C=CC=CC=1>[Cl:3][CH2:22][C:21]1[CH:24]=[CH:25][C:18]([O:17][CH2:16][C:14]2[N:15]=[C:11]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)[S:12][CH:13]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 688882164-(2-Phenyl-4-thiazolylmethoxy)benzyl alcohol

Product 1

HCID 178613834-(4-Chloromethylphenoxy)methyl-2-phenylthiazoleYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of thionyl chloride (1.5 ml) in toluene (5 ml) was added to a mixture of 4-(2-phenyl-4-thiazolylmethoxy)benzyl alcohol (4.35 g), tetrahydrofuran (50 ml) and toluene (50 ml) under ice-cooling, which was stirred at room temperature for 2 hours. The reaction mixture was concentrated. The residue was dissolved in ethyl acetate, and the solution was washed with saturated aqueous sodium bicarbonate solution, then with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated to obtain colorless crystals of 4-(4-chloromethylphenoxymethyl)-2-phenylthiazole (4.10 g, yield 89%). Melting point: 98–99° C.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe solution was washed with saturated aqueous sodium bicarbonate solution
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8c5ae72a22e44b60afc9228b60ca63c6
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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