2-AMINO-5,6-DIHYDRO-1,3-BENZOTHIAZOL-7(4H)-ONE Chemical Properties

Melting point:

269-270 °C(Solv: ethyl acetate (141-78-6))

Boiling point:

376.0±11.0 °C(Predicted)

Density 

1.428±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

DMSO (Sparingly)

form 

Solid

pka

3.36±0.20(Predicted)

color 

Light Yellow

InChI

InChI=1S/C7H8N2OS/c8-7-9-4-2-1-3-5(10)6(4)11-7/h1-3H2,(H2,8,9)

InChIKey

JAZOMJIYYHHUBH-UHFFFAOYSA-N

SMILES

S1C2C(=O)CCCC=2N=C1N

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

HazardClass 

IRRITANT

2-AMINO-5,6-DIHYDRO-1,3-BENZOTHIAZOL-7(4H)-ONE Usage And Synthesis

Synthesis

Step ii: Synthesis of 2-amino-5,6-dihydrobenzo[d]thiazol-7(4H)-one To a 100 mL round bottom flask was added 2-bromo-1,3-cyclohexanedione (1.0 g, 5.23 mmol) and methanol (15 mL). Subsequently, thiourea (0.397 g, 5.23 mmol) and pyridine (0.412 g, 5.23 mmol) were added to the same flask. The reaction mixture was heated to reflux temperature and stirred for 4 hours. After completion of the reaction, the volatile solvent was removed by distillation under reduced pressure to give the crude product. The crude product was dissolved in water and stirred for 5 min to promote the formation of precipitate. The precipitate was collected by filtration and washed with distilled water to give the final 2-amino-5,6-dihydrobenzo[d]thiazol-7(4H)-one (0.8 g, 91% yield). Product characterization data: 1H NMR (300 MHz, DMSO-d6): δ 8.12 (brs, 2H), 2.69 (t, 2H), 2.38 (t, 2H), 2.02 (m, 2H). LC-MS (ESI): m/z 168.9 [M + H]+.

References

[1] Patent: WO2015/101928, 2015, A1. Location in patent: Page/Page column 100
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 5, p. 2136 - 2145
[3] Pharmaceutical Chemistry Journal, 1993, vol. 27, # 7, p. 500 - 503
[4] Khimiko-Farmatsevticheskii Zhurnal, 1993, vol. 27, # 7, p. 37 - 39
[5] Patent: WO2005/5438, 2005, A1. Location in patent: Page/Page column 36

2-AMINO-5,6-DIHYDRO-1,3-BENZOTHIAZOL-7(4H)-ONE(17583-10-7)Related Product Information

• N-(5,5-DIMETHYL-7-OXO-4,5,6-TRIHYDROBENZOTHIAZOL-2-YL)ETHANAMIDE
• 2-AMINO-5,5-DIMETHYL-5,6-DIHYDROBENZOTHIAZOL-7(4H)-ONE
• 2-AMINO-5-METHYL-4,5,6-TRIHYDROBENZOTHIAZOL-7-ONE
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• N-(5,5-DIMETHYL-7-OXO(4,5,6-TRIHYDROBENZOTHIAZOL-2-YL))-3-PYRIDYLFORMAMIDE
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• N-(5-METHYL-7-OXO(4,5,6-TRIHYDROBENZOTHIAZOL-2-YL))(4-METHYLPHENYL)FORMAMIDE
• 2-AMINO-5-PHENYL-5,6-DIHYDRO-1,3-BENZOTHIAZOL-7(4H)-ONE
• N-(5,5-DIMETHYL-7-OXO(4,5,6-TRIHYDROBENZOTHIAZOL-2-YL))-4-METHYLPENT-2-ENAMIDE
• N-(5-METHYL-7-OXO(4,5,6-TRIHYDROBENZOTHIAZOL-2-YL))(2-PHENOXY(3-PYRIDYL))FORMAMIDE
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• N-(5,5-DIMETHYL-7-OXO(4,5,6-TRIHYDROBENZOTHIAZOL-2-YL))-2-(4-CHLOROPHENYLTHIO)PROPANAMIDE
• N-(7-OXO-5-PHENYL-4,5,6-TRIHYDROBENZOTHIAZOL-2-YL)ETHANAMIDE
• (2-CHLORO(3-PYRIDYL))-N-(5-METHYL-7-OXO(4,5,6-TRIHYDROBENZOTHIAZOL-2-YL))FORMAMIDE