Water → Methyl 3-(5-methyl-2-phenyl-4-thiazolylmethoxy)-5-isoxazolecarboxylate

HRID 1294152Notes

Reaction equation

HRID 1294152 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[O:4][N:3]=1.[H-].[Na+].Cl[CH2:14][C:15]1[N:16]=[C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[S:18][C:19]=1[CH3:20].O>CN(C)C=O>[CH3:20][C:19]1[S:18][C:17]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[N:16][C:15]=1[CH2:14][O:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[O:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 12794636Thiazole, 4-(chloromethyl)-5-methyl-2-phenyl-HCID 178498603HCID 178498603, compound

Product 1

HCID 17861290Methyl 3-(5-methyl-2-phenyl-4-thiazolylmethoxy)-5-isoxazolecarboxylateYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 3-hydroxyisoxazole-5-carboxylate (3.51 g) in N,N-dimethylformamide (100 mL) was added sodium hydride (60%, oil, 1.07 g) at 0° C. After stirring for 30 min., 4-chloromethyl-5-methyl-2-phenylthiazole (5.00 g) was added. After stirring at 60° C. for 2 hrs, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to give methyl 3-(5-methyl-2-phenyl-4-thiazolylmethoxy)-5-isoxazolecarboxylate (5.42 g, 74%) as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:4, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 89-90° C.

Workup

  1. stirringAfter stirring at 60° C. for 2 hrs
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d2375b715f6b42aba2597c1664665fbe
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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