(3-(2-chloro-6-fluorophenyl)-5-methylisoxazol-4-yl)methanol
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: (3-(2-chloro-6-fluorophenyl)-5-methylisoxazol-4-yl)methanol With potassium permanganate; disodium hydrogenphosphate In methanol; water at 25℃; Continuous flow conditions; Sonication; Stage #2: With hydrogenchloride; sodium thiosulfate; sodium chloride In methanol; water; ethyl acetate | 87% |
2-chloro-6-fluoro-N-hydroxybenzene-1-carbonimidoyl chloride
acetoacetic acid methyl ester
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
Conditions | Yield |
---|---|
With ethanol; triethylamine at 5℃; | 72% |
methyl 3-(2-chloro-6-fluorophenyl)-5-methylisoxazole-4-carboxylate
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol | |
With water; sodium hydroxide In methanol for 1h; pH=11 - 13; Reflux; | |
With water; sodium hydroxide In ethanol at 60℃; for 24h; | |
With sodium hydroxide In water for 3h; |
2-chloro-6-fluorobenzaldehyde
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: (i) NH2OH, (ii) Cl2, CHCl3, (iii) /BRN= 506727/, MeOH 2: aq. KOH / ethanol View Scheme | |
Multi-step reaction with 4 steps 1.1: hydroxylamine sulfate / methanol / 0.5 h 1.2: 0.5 h / pH 8 - 9 / Reflux 2.1: chlorine / methanol / 0 - 5 °C 3.1: sodium hydroxide / methanol / 0.5 h / 0 - 5 °C / pH 10 3.2: 2 h / 0 - 20 °C / pH 9 4.1: water; sodium hydroxide / methanol / 1 h / pH 11 - 13 / Reflux View Scheme | |
Multi-step reaction with 3 steps 1: sodium carbonate; hydroxylamine hydrochloride / ethanol; water / 2 h / 20 °C 2: pyridine; N-chloro-succinimide / chloroform / 1.5 h / 20 °C 3: ethanol; triethylamine / 5 °C View Scheme |
2-chloro-6-fluoro-N-hydroxybenzene-1-carbonimidoyl chloride
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium hydroxide / methanol / 0.5 h / 0 - 5 °C / pH 10 1.2: 2 h / 0 - 20 °C / pH 9 2.1: water; sodium hydroxide / methanol / 1 h / pH 11 - 13 / Reflux View Scheme |
N-[(2-chloro-6-fluorophenyl)methylidene]hydroxylamine
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: chlorine / methanol / 0 - 5 °C 2.1: sodium hydroxide / methanol / 0.5 h / 0 - 5 °C / pH 10 2.2: 2 h / 0 - 20 °C / pH 9 3.1: water; sodium hydroxide / methanol / 1 h / pH 11 - 13 / Reflux View Scheme | |
Multi-step reaction with 2 steps 1: pyridine; N-chloro-succinimide / chloroform / 1.5 h / 20 °C 2: ethanol; triethylamine / 5 °C View Scheme |
2-chloro-6-fluorobenzaldehyde
acetoacetic acid methyl ester
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: 2-chloro-6-fluorobenzaldehyde With hydroxylamine sulfate In methanol at 20 - 40℃; for 1h; Stage #2: With chlorine; sodium carbonate; triethylamine In methanol at 0 - 20℃; for 24h; pH=~ 9.5; Inert atmosphere; Stage #3: acetoacetic acid methyl ester With sodium carbonate In methanol pH=~ 7 - 7.5; |
ethyl 3-(2-chloro-6-fluorophenyl)-5-methylisoxazole-4-carboxylate
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
Conditions | Yield |
---|---|
With water; sodium hydroxide In ethanol at 60℃; for 24h; |
floxacillin
A
carbon dioxide
C
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
Conditions | Yield |
---|---|
With potassium tellurite; sulfuric acid at 14.84℃; Kinetics; Thermodynamic data; Temperature; |
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
Conditions | Yield |
---|---|
With phosphorus pentachloride at 45℃; for 1h; | 88% |
With phosphorus pentachloride In toluene | |
With phosphorus pentachloride In toluene |
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
3-(2-chloro-6-fluorophenyl)-5-methylisoxazole-4-carboxamide
Conditions | Yield |
---|---|
(i) SOCl2, (ii) NH3, acetone; Multistep reaction; | |
Multi-step reaction with 2 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / Reflux 2: sodium carbonate; ammonium hydroxide / water; diethyl ether / 3.17 h / 0 - 25 °C View Scheme |
(2-chloro-6-fluorophenyl)methanol
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
(2-chloro-6-fluoro-phenyl)methyl N-(3-(2-chloro-6-fluoro-phenyl)-5-methyl-1,2-oxazol-4-yl)carbamate
Conditions | Yield |
---|---|
With diphenyl phosphoryl azide; triethylamine In 1,4-dioxane Heating; |
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
Prop-2-ynyl 3-(2-chloro-6-fluorophenyl)-5-methylisoxazole-4-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: phosphorus pentachloride / 1 h / 45 °C 2: triethylamine / dichloromethane / 2 h / 0 - 20 °C View Scheme |
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
(1-(2-morpholino-2-oxoethyl)-1H-1,2,3-triazol-4-yl)methyl 3-(2-chloro-6-fluorophenyl)-5-methylisoxazole-4-caroboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: phosphorus pentachloride / 1 h / 45 °C 2: triethylamine / dichloromethane / 2 h / 0 - 20 °C 3: copper(ll) sulfate pentahydrate; sodium L-ascorbate / water; tert-butyl alcohol / 20 °C View Scheme |
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
(1-benzyl-1H-1,2,3-triazol-4-yl)methyl 3-(2-chloro-6-fluorophenyl)-5-methylisoxazole-4-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: phosphorus pentachloride / 1 h / 45 °C 2: triethylamine / dichloromethane / 2 h / 0 - 20 °C 3: copper(ll) sulfate pentahydrate; sodium L-ascorbate / water; tert-butyl alcohol / 20 °C View Scheme |
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
(1-(4-(1,3-dioxoisoindolin-2-yl)butyl)-1H-1,2,3-triazol-4-yl)methyl 3-(2-chloro-6-fluorophenyl)-5-methylisoxazole-4-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: phosphorus pentachloride / 1 h / 45 °C 2: triethylamine / dichloromethane / 2 h / 0 - 20 °C 3: copper(ll) sulfate pentahydrate; sodium L-ascorbate / water; tert-butyl alcohol / 20 °C View Scheme |
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
(1-butyl-1H-1,2,3-triazol-4yl)methyl 3-(2-chloro-6-fluorophenyl)-5-methylisoxazole-4-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: phosphorus pentachloride / 1 h / 45 °C 2: triethylamine / dichloromethane / 2 h / 0 - 20 °C 3: copper(ll) sulfate pentahydrate; sodium L-ascorbate / water; tert-butyl alcohol / 20 °C View Scheme |
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
(1-allyl-1H-1,2,3-triazol-4-yl)methyl 3-(2-chloro-6-fluorophenyl)-5-methylisoxazole-4 carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: phosphorus pentachloride / 1 h / 45 °C 2: triethylamine / dichloromethane / 2 h / 0 - 20 °C 3: copper(ll) sulfate pentahydrate; sodium L-ascorbate / water; tert-butyl alcohol / 20 °C View Scheme |
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0.67 h / -5 - 0 °C 2.1: 30 - 35 °C 2.2: 1 h / -5 - 0 °C View Scheme |
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
Flucloxacillin sodium
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 0.67 h / -5 - 0 °C 2.1: 30 - 35 °C 2.2: 1 h / -5 - 0 °C 3.1: sodium isooctanoate / acetone; water; ethyl acetate / 3 h / 20 - 25 °C View Scheme |
pivaloyl chloride
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at -5 - 0℃; for 0.666667h; Time; |
di(benzothiazol-2-yl)disulfide
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
Conditions | Yield |
---|---|
With triethylamine; triethyl phosphite In dichloromethane at 5 - 15℃; Large scale; |
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / Reflux 2: sodium carbonate; ammonium hydroxide / water; diethyl ether / 3.17 h / 0 - 25 °C 3: Lawessons reagent / 1,4-dioxane / 4 h / Reflux View Scheme |
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / Reflux 2: sodium carbonate; ammonium hydroxide / water; diethyl ether / 3.17 h / 0 - 25 °C 3: Lawessons reagent / 1,4-dioxane / 4 h / Reflux 4: water / 24 h / Reflux View Scheme |
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: 3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid With thionyl chloride for 3h; Reflux; Stage #2: With hydrazine hydrate In 1,4-dioxane at 25℃; for 2h; |
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: thionyl chloride / 3 h / Reflux 1.2: 2 h / 25 °C 2.1: 6 h / 140 °C / Microwave irradiation View Scheme |
thiazolidine-2-one
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: 3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.333333h; Stage #2: thiazolidine-2-one In dichloromethane at 20℃; |
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 40 °C 2: potassium carbonate / toluene / 0.42 h / 40 °C / Microwave irradiation View Scheme |
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 40 °C 2: potassium carbonate / toluene / 0.42 h / 40 °C / Microwave irradiation View Scheme |
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