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90533-23-6

90533-23-6 Structure

90533-23-6 Structure
IdentificationBack Directory
[Name]

4-(3-Chloro-phenyl)-thiazol-2-ylamine
[CAS]

90533-23-6
[Synonyms]

4-(3-Chlorophenyl)thiazol-2-amine
4-(3-Chlorophenyl)-2-thiazolamine
2-Thiazolamine, 4-(3-chlorophenyl)-
1-(3-chloro-5-fluorophenyl)-3-buten-1-ol
[Molecular Formula]

C9H7ClN2S
[MDL Number]

MFCD02664012
[MOL File]

90533-23-6.mol
[Molecular Weight]

210.68
Chemical PropertiesBack Directory
[Melting point ]

112 °C(Solv: ethanol (64-17-5))
[Boiling point ]

394.2±17.0 °C(Predicted)
[density ]

1.389±0.06 g/cm3(Predicted)
[storage temp. ]

Keep in dark place,Inert atmosphere,Room temperature
[pka]

3.94±0.10(Predicted)
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
Hazard InformationBack Directory
[Synthesis]

Carbamimidothioic acid

17356-08-0

3'-Chloroacetophenone

99-02-5

4-(3-Chloro-phenyl)-thiazol-2-ylamine

90533-23-6

The reaction mixture was stirred at 100 °C for 8 hours with thiourea (50 mmol), 3-chloroacetophenone (25 mmol) and iodine (25 mmol). After completion of the reaction, the mixture was cooled and extracted with ether to remove unreacted 3-chloroacetophenone. Subsequently, it was washed with aqueous sodium thiosulfate to remove excess iodine and then with cold water. The crude product was dissolved in hot water and filtered to remove the sulfone by-product. The filtrate was alkalized with aqueous Na2CO3 to afford 2-amino-4-(3-chlorophenyl)-1,3-thiazole. Finally, the crude product was purified by recrystallization from alcohol.

[References]

[1] Chemical and Pharmaceutical Bulletin, 2007, vol. 55, # 7, p. 1014 - 1017
[2] European Journal of Medicinal Chemistry, 2013, vol. 66, p. 305 - 313
[3] Arzneimittel-Forschung/Drug Research, 1986, vol. 36, # 9, p. 1391 - 1393
[4] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 2, p. 692 - 702
[5] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 23, p. 5428 - 5431
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