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160844-75-7

Basic Information
CAS No.: 160844-75-7
Name: 5-Thiazolecarboxylicacid, 2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-, ethyl ester
Molecular Structure:
Molecular Structure of 160844-75-7 (5-Thiazolecarboxylicacid, 2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-, ethyl ester)
Formula: C18H20N2O3S
Molecular Weight: 344.43
Synonyms: Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate;
EINECS: -0
Density: 1.22 g/cm3
Melting Point: 176 °C
Boiling Point: 497.149 °C at 760 mmHg
Flash Point: 254.467 °C
Solubility:
Appearance:
Hazard Symbols:
Risk Codes:
Safety:
Transport Information:
PSA: 100.45000
LogP: 4.20168
Synthetic route
876918-26-2

5-bromo-2-isobutoxy-benzonitrile

20582-55-2

ethyl 4-methylthiazole-5-carboxylate

A

1240593-43-4

C22H24N2O2

B

3944-31-8

diethyl 4,4-dimethyl-2,2-bithiazole-5,5-dicarboxylate

C

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
With di-tert-butyl(cyclohexyl)phosphine; potassium carbonate; palladium dichloride In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 24h; Reagent/catalyst; Inert atmosphere;A n/a
B n/a
C 100%
With potassium carbonate; di-tert-butyl(cyclohexyl)phosphine; palladium diacetate In xylene at 120℃; for 5h; Product distribution / selectivity; Inert atmosphere;
144060-96-8

2-(3-bromo-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

copper(l) cyanide

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
With copper(l) iodide In N,N-dimethyl-formamide at 130 - 140℃; for 16h;98.5%
78-77-3

Isobutyl bromide

161798-02-3

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In ethyl acetate at 65 - 70℃; for 5h; Temperature; Solvent; Reagent/catalyst;98.2%
With potassium carbonate In N,N-dimethyl-formamide at 75℃; for 8h;92.9%
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 90℃; for 3h;88%
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 90℃; for 3h;88%
With potassium carbonate In N,N-dimethyl-formamide at 75℃; for 15h;2.28 g
161798-03-4

2-(3-formyl-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
With ammonium hydroxide; sodium persulfate; sodium iodide; iron(II) chloride In 1,2-dichloro-ethane at 20 - 50℃; for 16h; Reagent/catalyst; Solvent; Temperature;98%
With hydroxylamine hydrochloride; sodium formate In formic acid for 3h; Product distribution / selectivity; Reflux;96%
With formic acid; hydroxylamine hydrochloride; sodium formate at 100℃; for 7h;95.2%
876918-26-2

5-bromo-2-isobutoxy-benzonitrile

20582-55-2

ethyl 4-methylthiazole-5-carboxylate

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
With di-tert-butyl(cyclohexyl)phosphine; potassium hydrogencarbonate; isobutyric Acid; copper(I) bromide; palladium dichloride In toluene at 25℃; for 21h; Reagent/catalyst; Time; Inert atmosphere; Reflux;93%
With potassium carbonate; di-tert-butyl(cyclohexyl)phosphine; palladium diacetate In xylene at 20℃; for 24.5h; Product distribution / selectivity; Reflux;82%
With di-tert-butyl(cyclohexyl)phosphine; copper(I) bromide dimethylsulfide complex; potassium carbonate; isobutyric Acid; palladium dichloride In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 24h; Inert atmosphere; Sealed tube;98.2 %Chromat.
20582-55-2

ethyl 4-methylthiazole-5-carboxylate

78-83-1

2-methyl-propan-1-ol

179897-89-3

5-Bromo-2-fluoro-benzonitrile

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
Stage #1: 2-methyl-propan-1-ol With potassium tert-butylate In toluene
Stage #2: 5-Bromo-2-fluoro-benzonitrile at 20℃; for 2h;
Stage #3: ethyl 4-methylthiazole-5-carboxylate With di-tert-butyl(cyclohexyl)phosphine; potassium hydrogencarbonate; isobutyric Acid; copper(I) bromide; palladium dichloride In toluene for 15h; Inert atmosphere; Reflux;
91%
105-39-5

chloroacetic acid ethyl ester

163597-57-7

3-cyanoisobutoxybenzothioamide

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
In ethanol at 100℃; for 2h;85%
78-77-3

Isobutyl bromide

161798-01-2

ethyl 2‐(3‐formyl‐4‐hydroxyphenyl)‐4‐methylthiazole‐5‐carboxylate

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
Stage #1: ethyl 2‐(3‐formyl‐4‐hydroxyphenyl)‐4‐methylthiazole‐5‐carboxylate With hydroxylamine hydrochloride In dimethyl sulfoxide at 40℃; for 0.5h;
Stage #2: With acetyl chloride In dimethyl sulfoxide at 70 - 80℃;
Stage #3: Isobutyl bromide With potassium carbonate In dimethyl sulfoxide at 20 - 80℃;
84%
Stage #1: ethyl 2‐(3‐formyl‐4‐hydroxyphenyl)‐4‐methylthiazole‐5‐carboxylate With hydroxylamine hydrochloride In dimethyl sulfoxide for 0.5h;
Stage #2: With acetyl chloride In dimethyl sulfoxide at 70 - 80℃;
Stage #3: Isobutyl bromide With potassium carbonate In dimethyl sulfoxide at 70 - 80℃; for 5h;
84%
161797-99-5

(2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester)

78-77-3

Isobutyl bromide

68-12-2, 33513-42-7

N,N-dimethyl-formamide

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
Stage #1: (2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester); Isobutyl bromide; N,N-dimethyl-formamide With potassium carbonate at 90 - 95℃;
Stage #2: With trichlorophosphate at 0 - 60℃; for 2h;
Stage #3: With ammonia; iodine at 10 - 20℃; for 2h; Temperature; Solvent;
83%
876918-26-2

5-bromo-2-isobutoxy-benzonitrile

2-boronic acid-4-methyl-1,3-thiazole-5-carboxylic acid ethyl ester

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 80℃; for 12h; Reagent/catalyst; Temperature; Suzuki Coupling; Inert atmosphere; Green chemistry;79%
22900-83-0

ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate

1139901-87-3

5-iodo-2-isobutoxy-benzonitrile

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 20℃; for 36h; Reagent/catalyst; Solvent;61%
609-15-4

ethyl 2-chloro-3-oxo-butyrate

163597-57-7

3-cyanoisobutoxybenzothioamide

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
In ethanol at 100℃; for 2h;306 mg
In toluene Product distribution / selectivity; Reflux;
In ethyl acetate; N,N-dimethyl-formamide at 80 - 85℃; for 22h;
In ethanol for 5h; Reflux;
161718-81-6

4-isobutoxyisophthalonitrile

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / thioacetamide, HCl / dimethylformamide / 40 h / 45 °C
2: 306 mg / ethanol / 2 h / 100 °C
View Scheme
Multi-step reaction with 2 steps
1: hydrogenchloride; thioacetamide / isopropyl alcohol / 14 h / 40 - 45 °C
2: ethyl acetate; N,N-dimethyl-formamide / 22 h / 80 - 85 °C
View Scheme
619-72-7

4-nitrobenzonitrile

methylmagnesium halide

methylmagnesium halide

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 2.) K2CO3 / 1.) DMSO, 100 deg C, 1 h, 2.) 6 h; 70 deg C
2: 85 percent / thioacetamide, HCl / dimethylformamide / 40 h / 45 °C
3: 306 mg / ethanol / 2 h / 100 °C
View Scheme
144060-96-8

2-(3-bromo-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

potassium ferrocyanide trihydrate

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
With sodium carbonate; palladium diacetate In 1-methyl-pyrrolidin-2-one at 145℃; for 48h; Inert atmosphere;
161798-01-2

ethyl 2‐(3‐formyl‐4‐hydroxyphenyl)‐4‐methylthiazole‐5‐carboxylate

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 4 h / 70 °C
2: hydroxylamine hydrochloride; sodium formate / formic acid / 3 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 0.5 h / 70 - 75 °C
1.2: 5 h
2.1: hydroxylamine hydrochloride; sodium formate; formic acid / 100 °C
View Scheme
Multi-step reaction with 2 steps
1: hydroxylamine hydrochloride; sodium formate; formic acid / 8 h / 100 °C
2: potassium carbonate / N,N-dimethyl-formamide / 8 h / 75 °C
View Scheme
609-15-4

ethyl 2-chloro-3-oxo-butyrate

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ethanol / 0.25 h / 70 °C
2: copper(ll) bromide; tert.-butylnitrite / acetonitrile / 1 h / 60 °C
3: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; water / 1 h / 70 - 75 °C
View Scheme
Multi-step reaction with 4 steps
1: spirit / 2.5 h / 60 - 65 °C
2: methanesulfonic acid / 10 h / 75 °C
3: hydroxylamine hydrochloride; sodium formate; formic acid / 8 h / 100 °C
4: potassium carbonate / N,N-dimethyl-formamide / 8 h / 75 °C
View Scheme
Multi-step reaction with 4 steps
1.1: isopropyl alcohol / 25 - 85 °C
2.1: trifluoroacetic acid / 24 h / 80 °C
2.2: 0.17 h
3.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 5.08 h / 25 - 85 °C
4.1: sodium formate; formic acid; hydroxylamine / 2.17 h / 25 - 100 °C
View Scheme
1761-61-1

5-bromosalicyclaldehyde

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 75 - 80 °C
2.1: hydroxylamine hydrochloride; sodium formate / formic acid / 7 h / 99 - 100 °C
3.1: n-butyllithium / hexane; tetrahydrofuran / 3 h / -45 - -40 °C
3.2: -20 °C
4.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; water / 1 h / 70 - 75 °C
View Scheme
876918-32-0

(3-cyano-4-isobutoxyphenyl)boronic acid

22900-83-0

ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 70 - 75℃; for 1h;
7210-76-6

ethyl-2-amino-4-methylthiazole-5-carboxylate

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: copper(ll) bromide; tert.-butylnitrite / acetonitrile / 1 h / 60 °C
2: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; water / 1 h / 70 - 75 °C
View Scheme
222315-01-7

5-bromo-2-isobutoxybenzaldehyde

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydroxylamine hydrochloride; sodium formate / formic acid / 7 h / 99 - 100 °C
2.1: n-butyllithium / hexane; tetrahydrofuran / 3 h / -45 - -40 °C
2.2: -20 °C
3.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; water / 1 h / 70 - 75 °C
View Scheme
876918-26-2

5-bromo-2-isobutoxy-benzonitrile

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: n-butyllithium / hexane; tetrahydrofuran / 3 h / -45 - -40 °C
1.2: -20 °C
2.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; water / 1 h / 70 - 75 °C
View Scheme
767-00-0

4-cyanophenol

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: N-Bromosuccinimide; trifluorormethanesulfonic acid / acetonitrile / -15 - 30 °C
2: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 12 h / 70 - 75 °C
3: sodium carbonate / palladium diacetate / N,N-dimethyl-formamide / 18 h / 140 - 145 °C
4: hydrogenchloride; thioacetamide / isopropyl alcohol / 14 h / 40 - 45 °C
5: ethyl acetate; N,N-dimethyl-formamide / 22 h / 80 - 85 °C
View Scheme
Multi-step reaction with 7 steps
1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 6 h / 80 °C
2: aluminum (III) chloride / nitromethane / 5.5 h / 0 - 5 °C
3: iron(III) sulfate; water / toluene / 0.7 h / 110 °C
4: tetrabutylammomium bromide; sodium hypochlorite / ethyl acetate; water / 0 - 5 °C
5: sodium hydrogen sulfide; magnesium(II) chloride hexahydrate / N,N-dimethyl-formamide / 4 h / 80 °C
6: N,N-dimethyl-formamide / 4 h / 60 °C
7: hydroxylamine hydrochloride; sodium formate; formic acid / 4.17 h / 25 - 100 °C
View Scheme
Multi-step reaction with 7 steps
1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 6 h / 80 °C
2: aluminum (III) chloride / nitromethane / 5.5 h / 0 °C
3: iron(III) sulfate; water / toluene / 0.7 h / 110 °C
4: tetrabutylammomium bromide; sodium hypochlorite / ethyl acetate; water / 0 - 5 °C
5: sodium hydrogen sulfide; magnesium(II) chloride hexahydrate / N,N-dimethyl-formamide / 4 h / 80 °C
6: N,N-dimethyl-formamide / 4 h / 60 °C
7: hydroxylamine hydrochloride; sodium formate; formic acid / 4.17 h / 25 - 100 °C
View Scheme
615-58-7

2,4-dibromophenol

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: palladium diacetate / dimethyl sulfoxide / 4 h / 40 - 45 °C
2: potassium carbonate; potassium iodide / dimethyl sulfoxide / 16 h / 70 - 75 °C
3: hydrogenchloride; thioacetamide / isopropyl alcohol / 14 h / 40 - 45 °C
4: ethyl acetate; N,N-dimethyl-formamide / 22 h / 80 - 85 °C
View Scheme
Multi-step reaction with 4 steps
1: sodium carbonate / palladium diacetate / N,N-dimethyl-formamide / 18 h / 140 - 145 °C
2: potassium carbonate; potassium iodide / dimethyl sulfoxide / 16 h / 70 - 75 °C
3: hydrogenchloride; thioacetamide / isopropyl alcohol / 14 h / 40 - 45 °C
4: ethyl acetate; N,N-dimethyl-formamide / 22 h / 80 - 85 °C
View Scheme
2315-86-8

3-bromo-4-hydroxybenzonitrile

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 12 h / 70 - 75 °C
2: sodium carbonate / palladium diacetate / N,N-dimethyl-formamide / 18 h / 140 - 145 °C
3: hydrogenchloride; thioacetamide / isopropyl alcohol / 14 h / 40 - 45 °C
4: ethyl acetate; N,N-dimethyl-formamide / 22 h / 80 - 85 °C
View Scheme
Multi-step reaction with 4 steps
1.1: hydrogenchloride / isopropyl alcohol / 0.25 h
1.2: 2 h / 50 - 55 °C
2.1: isopropyl alcohol / 5 h / 80 - 85 °C
3.1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 80 - 85 °C
4.1: copper(l) iodide / N,N-dimethyl-formamide / 16 h / 130 - 140 °C
View Scheme
34133-58-9

4-hydroxy-isophthalonitrile

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate; potassium iodide / dimethyl sulfoxide / 16 h / 70 - 75 °C
2: hydrogenchloride; thioacetamide / isopropyl alcohol / 14 h / 40 - 45 °C
3: ethyl acetate; N,N-dimethyl-formamide / 22 h / 80 - 85 °C
View Scheme
208665-95-6

3-bromo-4-isobutoxybenzonitrile

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium carbonate / palladium diacetate / N,N-dimethyl-formamide / 18 h / 140 - 145 °C
2: hydrogenchloride; thioacetamide / isopropyl alcohol / 14 h / 40 - 45 °C
3: ethyl acetate; N,N-dimethyl-formamide / 22 h / 80 - 85 °C
View Scheme
179897-89-3

5-Bromo-2-fluoro-benzonitrile

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C
1.2: 15 h / 0 - 20 °C
2.1: potassium carbonate / palladium diacetate; di-tert-butyl(cyclohexyl)phosphine / xylene / 24.5 h / 20 °C / Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydride / tetrahydrofuran; mineral oil / 4 h / 0 °C
1.2: 21 h / 0 - 20 °C
2.1: palladium dichloride; isobutyric Acid; di-tert-butyl(cyclohexyl)phosphine; potassium carbonate / 5,5-dimethyl-1,3-cyclohexadiene / 8 h / Reflux; Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydride / tetrahydrofuran; mineral oil / 4 h / 0 °C
1.2: 21 h / 0 - 20 °C
2.1: palladium dichloride; isobutyric Acid; copper(I) bromide dimethylsulfide complex; di-tert-butyl(cyclohexyl)phosphine; potassium carbonate / 5,5-dimethyl-1,3-cyclohexadiene / 24 h / 140 °C / Inert atmosphere; Sealed tube
View Scheme
179897-89-3

5-Bromo-2-fluoro-benzonitrile

A

1240593-43-4

C22H24N2O2

B

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C
1.2: 15 h / 0 - 20 °C
2.1: potassium carbonate / palladium diacetate; di-tert-butyl(cyclohexyl)phosphine / xylene / 5 h / 120 °C / Inert atmosphere
View Scheme
161797-99-5

(2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester)

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: methanesulfonic acid / 10 h / 75 °C
2: hydroxylamine hydrochloride; sodium formate; formic acid / 8 h / 100 °C
3: potassium carbonate / N,N-dimethyl-formamide / 8 h / 75 °C
View Scheme
Multi-step reaction with 3 steps
1: trifluoroacetic acid / 40 h / Reflux
2: potassium carbonate; N,N-dimethyl-formamide / 4 h / 87 - 93 °C
3: hydroxylamine hydrochloride; sodium formate; formic acid / 5 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: trifluoroacetic acid / 24 h / 80 °C
1.2: 0.17 h
2.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 5.08 h / 25 - 85 °C
3.1: sodium formate; formic acid; hydroxylamine / 2.17 h / 25 - 100 °C
View Scheme
160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carbohydrazide

Conditions
ConditionsYield
With hydrazine hydrate In ethanol for 5h; Reflux;99%
160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

febuxostat

Conditions
ConditionsYield
With water; sodium hydroxide In tetrahydrofuran; ethanol at 40℃; for 5h;98%
With methanol; sodium hydroxide In tetrahydrofuran at 20℃; for 5h; Green chemistry;96%
Stage #1: 2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester With water; sodium hydroxide In methanol at 45 - 60℃; for 1h;
Stage #2: With hydrogenchloride In methanol pH=2; Product distribution / selectivity;
95.8%
160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

1140907-13-6

febuxostat sodium

Conditions
ConditionsYield
With sodium hydroxide In water; isopropyl alcohol at 35 - 75℃; for 0.5h; Concentration; Temperature; Time;79%
160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

ethyl 4-methyl-2-(4-(2-methylpropyloxy)-3-cyanophenyl)-5-thiazolecarboxylate hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In acetone at 30 - 50℃; for 0.75h;61.5%
876918-32-0

(3-cyano-4-isobutoxyphenyl)boronic acid

160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

febuxostat

Conditions
ConditionsYield
Stage #1: (3-cyano-4-isobutoxyphenyl)boronic acid; 2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 70 - 75℃; for 1h;
Stage #2: With sodium hydroxide In tetrahydrofuran for 5h; Inert atmosphere; Reflux;
Stage #3: With hydrogenchloride In water
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  • 5-Thiazolecarboxylicacid, 2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-, ethyl ester

  • Casno:

    160844-75-7

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Specification

The Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate, with the CAS registry number 160844-75-7, is also known as 2-(3-Cyano-4-isobutoxy-phenyl)-4-methyl-thiazole-5-carboxylic acid ethyl ester. This chemical's molecular formula is C18H20N2O3S and molecular weight is 344.43. Its systematic name is called ethyl 2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylate.

Physical properties of Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate:
(1)ACD/LogP: 4.31; (2)ACD/LogD (pH 5.5): 6; (3)ACD/LogD (pH 7.4): 6; (4)ACD/BCF (pH 5.5): 12705; (5)ACD/BCF (pH 7.4): 12706; (6)ACD/KOC (pH 5.5): 30145; (7)ACD/KOC (pH 7.4): 30146; (8)#H bond acceptors: 5; (9)#Freely Rotating Bonds: 7; (10)Index of Refraction: 1.57; (11)Molar Refractivity: 92.567 cm3; (12)Molar Volume: 282.119 cm3; (13)Surface Tension: 53.922 dyne/cm; (14)Density: 1.221 g/cm3; (15)Flash Point: 254.467 °C; (16)Enthalpy of Vaporization: 76.506 kJ/mol; (17)Boiling Point: 497.149 °C at 760 mmHg; (18)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: N#Cc1c(OCC(C)C)ccc(c1)c2nc(c(s2)C(=O)OCC)C
(2)InChI: InChI=1/C18H20N2O3S/c1-5-22-18(21)16-12(4)20-17(24-16)13-6-7-15(14(8-13)9-19)23-10-11(2)3/h6-8,11H,5,10H2,1-4H3
(3)InChIKey: OGAZOYHQFBSRMC-UHFFFAOYAM.