• Name

  Ethionamide

• EINECS 208-628-9
• CAS No. 536-33-4
• Article Data29
• CAS DataBase
• Density 1.17 g/cm³
• Solubility Insoluble in water
• Melting Point 164 °C
• Formula C₈H₁₀N₂S
• Boiling Point 296.6 °C at 760 mmHg
• Molecular Weight 166.247
• Flash Point 133.2 °C
• Transport Information
• Appearance yellow solid
• Safety 36/37
• Risk Codes 22-63
• Molecular Structure
• Hazard Symbols Xn
• Synonyms Isonicotinamide,2-ethylthio- (6CI,8CI);Isonicotinimidic acid, 2-ethylthio- (7CI);1314TH;2-Ethyl-4-thiocarbamoylpyridine;2-Ethylisonicotinothioamide;2-Ethylthioisonicotinamide;Amidazine;Bayer 5312;Ethina;Etionamid;Etionizin;F.I. 58-30;IridocinBayer;NSC 255115;Sertinon;Thianid;Thioamide;Tianid;Trecator;Trekator;a-Ethylisothionicotinamide;
• PSA 71.00000
• LogP 1.97850

Synthetic route

3376-95-2

2-ethyl-4-pyridinecarboxamide

536-33-4

ethionamide

Conditions

Conditions	Yield
With pyridin-1-ium-1-yl[pyridin-1-ium-1-yl(sulfido)phosphinothioyl]sulfanyl-sulfido-thioxo-phosphane In acetonitrile for 0.5h; Reflux;	82%
With Lawessons reagent In tetrahydrofuran at 20℃; for 48h; Inert atmosphere;	35%
Multi-step reaction with 2 steps 1: POCl3 / 120 - 130 °C 2: ethanol; tris-<2-hydroxy-ethyl>-amine / Einleiten von H2S View Scheme

1531-18-6

2-ethyl-4-pyridinecarbonitrile

536-33-4

ethionamide

Conditions

Conditions	Yield
With 2,3,4,5,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium acetate; sodiumsulfide nonahydrate In neat (no solvent) at 20℃; for 2h; Green chemistry;	80%
Stage #1: 2-ethyl-4-pyridinecarbonitrile With magnesium chloride In N,N-dimethyl-formamide for 0.0833333h; Inert atmosphere; Stage #2: With sodium hydrogen sulfide In N,N-dimethyl-formamide at 20℃; for 2h;	70%
With sodiumsulfide nonahydrate In N,N-dimethyl-formamide at 130℃; for 2.5h;	67%
With triethanolamine; ethanol Einleiten von H2S;
With pyridine; triethylamine Einleiten von H2S;

1531-16-4

methyl 2-ethylpyridine-4-carboxylate

536-33-4

ethionamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: aqueous NH3 2: POCl3 / 120 - 130 °C 3: ethanol; tris-<2-hydroxy-ethyl>-amine / Einleiten von H2S View Scheme

4104-77-2

2-ethyl-6-chloro-isonicotinic acid methyl ester

536-33-4

ethionamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: palladium/charcoal; methanol; potassium acetate / Hydrogenation 2: aqueous NH3 3: POCl3 / 120 - 130 °C 4: ethanol; tris-<2-hydroxy-ethyl>-amine / Einleiten von H2S View Scheme

156761-88-5

4-bromo-2-ethyl-pyridine

536-33-4

ethionamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 160 - 170 °C 2: pyridine; triethylamine / Einleiten von H2S View Scheme

50826-64-7

4-amino-2-ethylpyridine

536-33-4

ethionamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: bromine; aqueous sodium nitrite solution; aqueous hydrobromic acid 2: 160 - 170 °C 3: pyridine; triethylamine / Einleiten von H2S View Scheme

4833-24-3

2-ethylpyridine 1-oxide

536-33-4

ethionamide

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: sulfuric acid; nitric acid 2: iron; concentrated aqueous HCl; acetic acid 3: bromine; aqueous sodium nitrite solution; aqueous hydrobromic acid 4: 160 - 170 °C 5: pyridine; triethylamine / Einleiten von H2S View Scheme

38594-62-6

2-ethyl-4-nitropyridine 1-oxide

536-33-4

ethionamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: iron; concentrated aqueous HCl; acetic acid 2: bromine; aqueous sodium nitrite solution; aqueous hydrobromic acid 3: 160 - 170 °C 4: pyridine; triethylamine / Einleiten von H2S View Scheme

100-48-1

pyridine-4-carbonitrile

536-33-4

ethionamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sulfuric acid; silver nitrate; ammonium persulfate / water / 0.33 h / 70 °C 2.1: magnesium chloride / N,N-dimethyl-formamide / 0.08 h / Inert atmosphere 2.2: 2 h / 20 °C View Scheme

29840-73-1

2-bromopyridine-4-carboxamide

536-33-4

ethionamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 0 - 20 °C / Schlenk technique; Inert atmosphere 2: Lawessons reagent / tetrahydrofuran / 48 h / 20 °C / Inert atmosphere View Scheme

536-33-4

ethionamide

1531-18-6

2-ethyl-4-pyridinecarbonitrile

Conditions

Conditions	Yield
With pyridine; aryl chlorothionoformate In dichloromethane for 5h; Ambient temperature;	95%
With di(n-butyl)tin oxide In toluene for 3h; Dehydration; Heating;	95%
With triethylamine; 2,2,2-Trichloroethyl chloroformate In dichloromethane at 0 - 20℃; Elimination;	92%

536-33-4

ethionamide

1694-29-7

3-chloropentane-2,4-dione

1-[2-(2-ethylpyridin-4-yl)-4-methylthiazol-5-yl]ethanone

Conditions

Conditions	Yield
In ethanol for 5h; Reflux;	92%

536-33-4

ethionamide

609-15-4

ethyl 2-chloro-3-oxo-butyrate

864684-98-0

ethyl 2-(2-ethyl-4-pyridyl)-4-methylthiazole-5-carboxylate

Conditions

Conditions	Yield
In ethanol for 5h; Reflux;	90%

536-33-4

ethionamide

536-38-9

4-chlorobenzoylmethyl bromide

125255-97-2

4-(4-chlorophenyl)-2-(ethylpyridin-4-yl)thiazole

Conditions

Conditions	Yield
In ethanol at 80℃;	82%

536-33-4

ethionamide

358-23-6

trifluoromethylsulfonic anhydride

685-87-0

Diethyl 2-bromomalonate

5-(ethoxycarbonyl)-2-(2-ethyl-4-pyridyl)-4-thiazolyl trifluoromethanesulfonate

Conditions

Conditions	Yield
Stage #1: ethionamide; Diethyl 2-bromomalonate With pyridine In ethanol for 3h; Reflux; Inert atmosphere; Stage #2: trifluoromethylsulfonic anhydride With pyridine In dichloromethane at 20℃; Cooling with ice; Inert atmosphere;	82%

...Expand

536-33-4

ethionamide

55203-23-1

3,5-bis(2-ethyl-4-pyridinyl)-1,2,4-thiadiazole

Conditions

Conditions	Yield
With copper(II) bis(trifluoromethanesulfonate); potassium carbonate In acetonitrile at 70℃; for 0.25h; chemoselective reaction;	78%

536-33-4

ethionamide

685-87-0

Diethyl 2-bromomalonate

74-88-4

methyl iodide

2-(2-ethyl-4-pyridyl)-4-methoxythiazole-5-carboxylic acid ethyl ester

Conditions

Conditions	Yield
Stage #1: ethionamide; Diethyl 2-bromomalonate With pyridine In ethanol for 3h; Reflux; Inert atmosphere; Stage #2: methyl iodide With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere;	65%

...Expand

536-33-4

ethionamide

(1-bromo-2-oxoethyl)MIDA boronate

(2-(2-ethylpyridin-4-yl)thiazol-5-yl)MIDA boronate

Conditions

Conditions	Yield
Stage #1: ethionamide; (1-bromo-2-oxoethyl)MIDA boronate In acetonitrile at 85℃; Stage #2: With Amberlite IRA-67 In acetonitrile at 20℃; for 0.5h; regioselective reaction;	64%

536-33-4

ethionamide

3376-95-2

2-ethyl-4-pyridinecarboxamide

Conditions

Conditions	Yield
With potassium superoxide; 18-crown-6 ether for 1h; Ambient temperature;	61%
With peracetic acid; sodium chloride at 25℃; Kinetics;

67-56-1

methanol

536-33-4

ethionamide

2-(2-ethylpyridin-4-yl)-4-(2-methoxypyridin-4-yl)thiazole

Conditions

Conditions	Yield
With sodium hydroxide at 120℃;	55.3%

536-33-4

ethionamide

533-68-6

2-bromobutyric acid ethyl ester

1429341-43-4

5-ethyl-2-(2-ethyl-pyridin-4-yl)-thiazol-4-ol

Conditions

Conditions	Yield
With pyridine In ethanol at 20℃; for 16h; Reflux;	17%
With pyridine In ethanol at 20℃; for 16h; Reflux;	17%

536-33-4

ethionamide

5714-80-7, 18598-63-5, 70361-61-4

cysteine methyl ester hydrochloride

104398-30-3

2-(2-ethyl-pyridin-4-yl)-4,5-dihydro-thiazole-4-carboxylic acid methyl ester

Conditions

Conditions	Yield
at 120℃; for 2h;

536-33-4

ethionamide

645418-40-2

1-(2-ethylpyridin-4-yl)methanamine

Conditions

Conditions	Yield
Raney 2800 nickel In methanol at 20 - 60℃; for 18h;
With nickel In methanol at 20 - 60℃;

536-33-4

ethionamide

727382-86-7

5-(2-Bromo-acetyl)-2-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid ethyl ester

727382-93-6

ethyl 5-[2-(2-ethyl-4-pyridyl)-1,3-thiazol-4-yl]-2-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate

Conditions

Conditions	Yield
In ethanol at 150℃; for 0.116667h;

536-33-4

ethionamide

521266-83-1

2-[2-(2-ethyl-pyridin-4-yl)-5-methyl-thiazol-4-yl]-ethanol

105983-77-5

methyl 4-bromo-3-oxopentanoate

521266-82-0

(2S)-1-({2-[2-(2-Ethyl-pyridin-4-yl)-5-methyl-thiazol-4-yl]-ethylamino}-acetyl)-pyrrolidine-2-carbonitrile

...Expand

536-33-4

ethionamide

fluorosilicic acid

bis(2-ethyl-4-thiocarbamoyl-4-pyridinium) hexafluorosilicate

Conditions

Conditions	Yield
In methanol dissolving of 2-ethyl-4-thiocarbamoyl-4-pyridine in MeOH, addn. of 45% silicahydrofluoric acid; evapn. at room temp., crystn.; elem. anal.;

536-33-4

ethionamide

2C8H10N2S*F6Si(2-)*2H(1+)

Conditions

Conditions	Yield
With fluorosilicic acid In methanol; water at 20℃;

536-33-4

ethionamide

1429341-44-5

trifluoro-methanesulfonic acid 5-ethyl-2-(2-ethyl-pyridin-4-yl)-thiazol-4-yl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: pyridine / ethanol / 16 h / 20 °C / Reflux 2.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C 2.2: 1 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: pyridine / ethanol / 16 h / 20 °C / Reflux 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / 0 °C 2.2: 1 h / 20 °C View Scheme

536-33-4

ethionamide

1589819-00-0

4-(2-bromoacetyl)-N-(3,3,3-trifluoropropyl)benzamide

4-(2-(2-ethylpyridin-4-yl)thiazol-4-yl)-N-(3,3,3-trifluoropropyl)benzamide

Conditions

Conditions	Yield
In tetrahydrofuran; diethyl ether

Ethinamide Chemical Properties

Ethinamide Uses

Ethinamide Production

Ethinamide Safety Profile