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With sodium hydroxide; potassium carbonate; In N-methyl-acetamide; ethanol; water;
Reference Example 1 A solution of o-isopropylphenol (39.5 g), potassium carbonate (40 g) and ethyl alpha-bromoacetate (40 ml) in dimethylformamide (300 ml) is heated with stirring at 80 C. for 8 hours. To the mixture is added water, and the mixture is extracted with ethyl acetate. The extract is washed with water, dried, and concentrated under reduced pressure to remove the solvent. The residue thus obtained is dissolved in a solution of sodium hydroxide (20 g) in water (300 ml) and ethanol (200 ml), and the mixture is refluxed for 1.5 hour. After cooling, the mixture is acidified with conc. hydrochloric acid, and the precipitated crystals are collected by filtration to give alpha-(2-isopropylphenoxy)acetic acid (37 g). White powder; 1 H-NMR (CDCl3) deltappm: 1.24 (6H, d, J=7 Hz), 3.39 (1H, sept, J=7 Hz), 4.69 (2H, s), 6.75 (1H, dd, J=1 Hz, J=8 Hz), 6.95-7.3 (3H, m).
2-(2-isopropylphenoxymethylcarbonylamino)benzothiazole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With pyridine; In thionyl chloride; ethanol; dichloromethane;
Reference Example 2 A solution of alpha-<strong>[25141-58-6](2-isopropylphenoxy)acetic acid</strong> (13.1 g) in thionyl chloride (30 ml) is refluxed for 30 minutes. The mixture is concentrated under reduce pressure to remove the excess thionyl chloride, and the resultant is dissolved in dichloromethane (50 ml). The mixture is added dropwise into a solution of 2-aminobenzothiazole (9.1 g) and pyridine (7.2 ml) in dichloromethane (100 ml) under ice-cooling. The mixture is stirred at the same temperature for five hours, and then washed with water, dried, and concentrated under reduced pressure. To the residue is added ethanol to give 2-(2-isopropylphenoxymethylcarbonylamino)benzothiazole (16.66 g). Yellow powder; 1 H-NMR (CDCl3) deltappm: 1.32 (6H, d, J=7 Hz) 3.43 (1H, sept, J=7 Hz), 4.78 (2H, s), 6.85 (1H, dd, J=1 Hz, J=8 Hz), 7.0-7.55 (5H, m), 7.8-7.9 (2H, m), 9.74 (1H, br).
General procedure: General procedure: To a solution of phenol or ring-substituted phenol (20 mmol) in water (20 mL) was added sodium chloroacetate (22 mmol) at rt. The mixture was heated and stirred at reflux for 8 h. The reaction mixture was cooled and the pH was adjusted to a value of 1.0 with 5 N HCl. The solution was filtered and the obtained solid was recrystallized from dehydrated ethanol to afford the pure product. 2-Isopropylphenoxyacetic acid (1c) Following the general procedure the compound 1c was obtained in 63 % yield as a white solid. m.p. 135-138 C. 1H NMR (400 MHz, CDCl3)delta 7.26 (d, J = 5.7 Hz, 1H), 7.15 (dd, J = 11.2, 4.3 Hz, 1H), 7.00(t, J = 7.5 Hz, 1H), 6.74 (d, J = 8.1 Hz, 1H), 4.70 (s, 2H), 3.39(hept, J = 6.9 Hz, 1H), 1.24 (d, J = 6.9Hz, 6H). MSESIm/z: 193 [M-H]-. (S2)
General procedure: Compounds (3a-j,0.02mol) were dissolved in ethanol (15mL), sodium hydroxide (0.035mol) in water (5mL) was added, and the mixture was refluxed for 5-9h. The reaction mixture was cooled and acidified with 2N hydrochloric acid. The precipitate was filtered, washed with water, and finally recrystallized from methanol to afford desired compounds (4a-j). Compound (4a) is takenas a representative example to explain physical and characterization data.
N-(4-(4-chlorophenyl) thiazol-2-yl)-2-(2-isopropylphenoxy)acetamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
General procedure: Phenoxyacetic acids (4a-j, 2mmol) in dry DCM (20ml) was stirred at 25-30C, and then lutidine (3mmol) was added, followed by the addition of substituted amino-4-phenyl-1,3-thiazoles (2mmol). The reaction mixture was stirred at the same temperature for 30min, then cooled to 0-5C and TBTU (2mmol) was added over a period of 30min maintaining the temperature below 5C. The reaction mass was stirred overnight and monitored by TLC using chloroform: methanol (9:1) as the mobile phase. The purity of the compounds was determined using high performance liquid chromatography (HPLC) by reversed phase agilent zorbax SB-C18 column method, with methanol (50%): acetonitrile (30%): water (20%) as mobile phase. The solvent was evaporated at reduced pressure, quenched by the addition of crushed ice and the obtained solid was filtered, dried and recrystallized from ethanol to afford compounds 8a-ab in good yield [supplementary files].
2-(2-isopropylphenoxy)-N-(4-(p-tolyl) thiazol-2-yl)acetamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
General procedure: Phenoxyacetic acids (4a-j, 2mmol) in dry DCM (20ml) was stirred at 25-30C, and then lutidine (3mmol) was added, followed by the addition of substituted amino-4-phenyl-1,3-thiazoles (2mmol). The reaction mixture was stirred at the same temperature for 30min, then cooled to 0-5C and TBTU (2mmol) was added over a period of 30min maintaining the temperature below 5C. The reaction mass was stirred overnight and monitored by TLC using chloroform: methanol (9:1) as the mobile phase. The purity of the compounds was determined using high performance liquid chromatography (HPLC) by reversed phase agilent zorbax SB-C18 column method, with methanol (50%): acetonitrile (30%): water (20%) as mobile phase. The solvent was evaporated at reduced pressure, quenched by the addition of crushed ice and the obtained solid was filtered, dried and recrystallized from ethanol to afford compounds 8a-ab in good yield [supplementary files].
N-(4-(4-bromophenyl) thiazol-2-yl)-2-(2-isopropylphenoxy)acetamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
General procedure: Phenoxyacetic acids (4a-j, 2mmol) in dry DCM (20ml) was stirred at 25-30C, and then lutidine (3mmol) was added, followed by the addition of substituted amino-4-phenyl-1,3-thiazoles (2mmol). The reaction mixture was stirred at the same temperature for 30min, then cooled to 0-5C and TBTU (2mmol) was added over a period of 30min maintaining the temperature below 5C. The reaction mass was stirred overnight and monitored by TLC using chloroform: methanol (9:1) as the mobile phase. The purity of the compounds was determined using high performance liquid chromatography (HPLC) by reversed phase agilent zorbax SB-C18 column method, with methanol (50%): acetonitrile (30%): water (20%) as mobile phase. The solvent was evaporated at reduced pressure, quenched by the addition of crushed ice and the obtained solid was filtered, dried and recrystallized from ethanol to afford compounds 8a-ab in good yield [supplementary files].
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