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Basic Information
CAS No.: 302964-24-5
Name: 2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide
Article Data: 32
Molecular Structure:
Molecular Structure of 302964-24-5 (2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide)
Formula: C11H10ClN3OS
Molecular Weight: 267.739
Synonyms: 2-Amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide;
EINECS: 1806241-263-5
Density: 1.474 g/cm3
Melting Point: 208.0 to 212.0 °C
Boiling Point: 362 °C at 760 mmHg
Flash Point: 172.7 °C
PSA: 96.25000
LogP: 3.59360
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Synthetic route

N-(2-chloro-6-methylphenyl)-3-ethoxyprop-2-enamide

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thiourea

302964-24-5

2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide

Conditions
ConditionsYield
Stage #1: N-(2-chloro-6-methylphenyl)-3-ethoxyprop-2-enamide With 1-butyl-3-methylimidazolium Tetrafluoroborate; copper(I) bromide In tetrahydrofuran for 0.5h;
Stage #2: thiourea In tetrahydrofuran at 40℃; for 1.5h; Temperature; Solvent; Reagent/catalyst;		98.9%
Stage #1: N-(2-chloro-6-methylphenyl)-3-ethoxyprop-2-enamide With N-Bromosuccinimide In 1,4-dioxane; water at 0 - 10℃;
Stage #2: thiourea In 1,4-dioxane; water at 20 - 80℃;		85 g
With N-Bromosuccinimide at -10 - 80℃;
863127-76-8

(E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide

17356-08-0

thiourea

302964-24-5

2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide

Conditions
ConditionsYield
Stage #1: (E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide With iodine(I) bromide; 1-n-butyl-3-methylimidazolim bromide In tetrahydrofuran at 40℃;
Stage #2: thiourea In tetrahydrofuran for 1.5h; Temperature; Concentration; Solvent; Reagent/catalyst;		98.8%
Stage #1: (E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide With N-Bromosuccinimide In 1,4-dioxane; water at -10 - 22℃; for 3h;
Stage #2: thiourea In 1,4-dioxane; water at 100℃; for 2h;
Stage #3: With ammonia In 1,4-dioxane; water at 20 - 22℃;		90%
Stage #1: (E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide With N-Bromosuccinimide In 1,4-dioxane at -10 - 22℃; for 3h;
Stage #2: thiourea In 1,4-dioxane at 100℃; for 2h;
Stage #3: With ammonium hydroxide In 1,4-dioxane; water at 20 - 22℃;		90%
Stage #1: (E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide With N-Bromosuccinimide In 1,4-dioxane; water at 25 - 30℃; for 3h;
Stage #2: thiourea In 1,4-dioxane; water at 25 - 70℃; for 2h;		213 g

C10H9BrClNO2

17356-08-0

thiourea

302964-24-5

2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide

Conditions
ConditionsYield
for 0.0611111h; Microwave irradiation;97.23%
at 20℃; for 1h;95.94%
In water at 20℃; for 2h; Solvent;95.94%
1044209-25-7

C10H10ClNO2

17356-08-0

thiourea

302964-24-5

2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide

Conditions
ConditionsYield
With copper(ll) bromide In tetrahydrofuran; water at 35 - 40℃; for 0.5h; Reagent/catalyst; Solvent;96.13%
17356-08-0

thiourea

302964-24-5

2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide

Conditions
ConditionsYield
Stage #1: (E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide With N-Bromosuccinimide In 1,4-dioxane; water at -10 - 22℃; for 3h;
Stage #2: thiourea In 1,4-dioxane; water at 80℃; for 2h;		94.9%
34780-29-5

3-oxo-propionic acid ethyl ester

17356-08-0

thiourea

87-63-8

2-chloro-6-methylaniline

302964-24-5

2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide

Conditions
ConditionsYield
Stage #1: 3-oxo-propionic acid ethyl ester With sodium methylate In tetrahydrofuran at 20℃; for 0.166667h;
Stage #2: 2-chloro-6-methylaniline In tetrahydrofuran for 0.75h; Reflux;
Stage #3: thiourea Solvent; Further stages;		92.31%
Stage #1: 3-oxo-propionic acid ethyl ester; 2-chloro-6-methylaniline With sodium methylate In tetrahydrofuran for 0.75h; Reflux;
Stage #2: With copper(ll) bromide In tetrahydrofuran for 1h; Reflux;
Stage #3: thiourea In tetrahydrofuran at 20 - 25℃; for 0.25h; Reagent/catalyst;		90.94%
...Expand
302964-06-3

[5-(2-chloro-6-methylphenylcarbamoyl)thiazol-2-yl]-carbamic acid tert-butyl ester

302964-24-5

2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide

Conditions
ConditionsYield
With trifluoroacetic acid at 25 - 30℃; for 2h;89%
With trifluoroacetic acid In dichloromethane at -5 - 20℃; for 10.5h;85%
With trifluoroacetic acid at 25 - 30℃; Reagent/catalyst; Temperature;78%

N-(2-chloro-6-methylphenyl)-2-(tritylamino)thiazole-5-carboxamide

302964-24-5

2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide

Conditions
ConditionsYield
With formic acid In ethanol Heating / reflux;70%
87-63-8

2-chloro-6-methylaniline

302964-24-5

2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: i-Pr2NEt / tetrahydrofuran
2: TFA / CH2Cl2
View Scheme
Multi-step reaction with 2 steps
1: pyridine / tetrahydrofuran
2: N-Bromosuccinimide / -10 - 80 °C
View Scheme
Multi-step reaction with 2 steps
1.1: sodium methylate / tetrahydrofuran / 0.17 h / 20 °C
1.2: 1 h / Reflux
1.3: 2 h / Reflux
2.1: water / 2 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: sodium methylate / tetrahydrofuran / 10 h / 20 °C
1.2: 1 h / Reflux
2.1: copper(ll) bromide / tetrahydrofuran; water / 0.5 h / 35 - 40 °C
View Scheme
Multi-step reaction with 2 steps
1.1: sodium methylate / tetrahydrofuran / 1 h / Reflux
1.2: 2 h / Reflux
2.1: 0.06 h / Microwave irradiation
View Scheme

2-chloro-N-(2-chloro-6-methyl-phenyl)-3,3-dimethoxy-propionamide

17356-08-0

thiourea

302964-24-5

2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide

Conditions
ConditionsYield
Stage #1: 2-chloro-N-(2-chloro-6-methyl-phenyl)-3,3-dimethoxy-propionamide; thiourea With hydrogenchloride; acetic acid at 50 - 65℃; for 11h; Industry scale;
Stage #2: With sodium methylate In methanol pH=8 - 9; Industry scale;
Raw Materials
302964-06-3
863127-76-8
87-63-8
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Specification

The systematic name of 2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide is 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide. With the CAS registry number 302964-24-5, it is also named as 5-Thiazolecarboxamide,2-amino-N-(2-chloro-6-methylphenyl)-. The product's categories are Dasatinib; API Intermediates. In addition, its molecular formula is C11H10ClN3OS and molecular weight is 267.73.

The other characteristics of 2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide can be summarized as: (1)ACD/LogP: 1.75; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.75; (4)ACD/LogD (pH 7.4): 1.75; (5)ACD/BCF (pH 5.5): 12.53; (6)ACD/BCF (pH 7.4): 12.58; (7)ACD/KOC (pH 5.5): 212.28; (8)ACD/KOC (pH 7.4): 213.21; (9)#H bond acceptors: 4; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 96.25 Å2; (13)Index of Refraction: 1.714; (14)Molar Refractivity: 71.26 cm3; (15)Molar Volume: 181.5 cm3; (16)Polarizability: 28.24×10-24cm3; (17)Surface Tension: 69.2 dyne/cm; (18)Density: 1.474 g/cm3; (19)Flash Point: 172.7 °C; (20)Enthalpy of Vaporization: 60.79 kJ/mol; (21)Boiling Point: 362 °C at 760 mmHg; (22)Vapour Pressure: 1.99E-05 mmHg at 25 °C.

People can use the following data to convert to the molecule structure.
(1)SMILES: O=C(Nc1c(C)cccc1Cl)c2cnc(N)s2
(2)InChI: InChI=1/C11H10ClN3OS/c1-6-3-2-4-7(12)9(6)15-10(16)8-5-14-11(13)17-8/h2-5H,1H3,(H2,13,14)(H,15,16)
(3)InChIKey: VVOXTERFTAJMAA-UHFFFAOYAL
(4)Std. InChI: InChI=1S/C11H10ClN3OS/c1-6-3-2-4-7(12)9(6)15-10(16)8-5-14-11(13)17-8/h2-5H,1H3,(H2,13,14)(H,15,16)
(5)Std. InChIKey: VVOXTERFTAJMAA-UHFFFAOYSA-N