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Chemical Structure| 333-20-0 Chemical Structure| 333-20-0

Structure of 333-20-0

Chemical Structure| 333-20-0

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Product Details of [ 333-20-0 ]

CAS No. :333-20-0
Formula : CKNS
M.W : 97.18
SMILES Code : [S-]C#N.[K+]
MDL No. :MFCD00011413
InChI Key :ZNNZYHKDIALBAK-UHFFFAOYSA-M
Pubchem ID :516872

Safety of [ 333-20-0 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H312-H332-H318-H401-H412
Precautionary Statements:P261-P264-P270-P271-P273-P280-P301+P312+P330-P302+P352+P310-P304+P340+P312-P305+P351+P338+P310-P501
Class:8
UN#:3261
Packing Group:

Application In Synthesis of [ 333-20-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 333-20-0 ]
  • Downstream synthetic route of [ 333-20-0 ]

[ 333-20-0 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 333-20-0 ]
  • [ 540-37-4 ]
  • [ 16582-58-4 ]
YieldReaction ConditionsOperation in experiment
70%
Stage #1: at 20℃; Cooling with ice
Stage #2: With ammonium hydroxide In water
General procedure: A mixture of 0.1 mol of 4-substituted aniline and 0.1 mol of Potassium thiocyanate (KCNS) in 100 ml glacial acetic acid (AcOH) was cooled in an ice bath and stirred for 10-20 min, and then 0.1 mol bromine in glacial acetic acid was added dropwise at such a rate to keep the temperature below 10 °C throughout the addition. The reaction mixture was stirred at room temperature for 2-4 h, the hydrobromide (HBr) salt thus separated out was filtered, washed with acetic acid, dried, dissolved in hot water and basified to pH 11.0 with ammonia solution (NH4OH) and the resulting precipitate was filtered, washed with water and dried to get the desired product 3a-k. The progress of the reaction was monitored by Thin Layer Chromatography using toluene: acetone (8:2) solvent system.
References: [1] European Journal of Medicinal Chemistry, 2012, vol. 53, p. 41 - 51.
[2] Heteroatom Chemistry, 2012, vol. 23, # 4, p. 399 - 410.
[3] European Journal of Medicinal Chemistry, 2014, vol. 71, p. 24 - 30.
[4] Medicinal Chemistry, 2013, vol. 9, # 4, p. 596 - 607.
[5] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 23, p. 5561 - 5565.
  • 2
  • [ 333-20-0 ]
  • [ 150-13-0 ]
  • [ 93-85-6 ]
References: [1] Synlett, 2012, vol. 23, # 15, p. 2219 - 2222.
[2] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1991, vol. 30, # 5, p. 494 - 498.
[3] Patent: WO2010/62171, 2010, A2, . Location in patent: Page/Page column 156.
[4] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 23, p. 5561 - 5565.
[5] Patent: KR2018/81285, 2018, A, . Location in patent: Paragraph 0132; 0144-0147.
  • 3
  • [ 333-20-0 ]
  • [ 88-74-4 ]
  • [ 6973-51-9 ]
YieldReaction ConditionsOperation in experiment
86%
Stage #1: With nano-BF3/SiO2 In acetonitrile for 0.5 h; Cooling with ice
Stage #2: With bromine In acetonitrile at 0 - 20℃; for 5 h;
General procedure: A solution of substituted aniline (2 mmol) in acetonitrile (15 ml) was added to a solution of KSCN (8 mmol) in acetonitrile (15 ml). Then, 0.06 g (30 mol percent BF3) of nano-BF3/SiO2 was added to the mixture, then was placed in a freezing mixture of ice and salt and mechanically stirred for 30 min. Then, bromine (4 mmol, 0.2 ml) in acetonitrile (3 ml) as solvent was added from a dropping funnel at such a rate that the temperature never rose beyond 0°C. After all the bromine was added at 60 min, the solution was stirred for 4 h at room temperature. The progress of the reaction was monitored by TLC. Then, the mixture was poured into water with stirring and the mixture was heated to 70°C on a steam bath and filtered hot to remove the catalyst and the recovered catalyst was washed with acetone and reused in the reaction. The filtrate was neutralized with 10 percent NaOH solution and the precipitate was collected on a filter, dried and recrystallized from ethanol (10 ml) to afford the corresponding products. All of the 2-aminobenzothiazole products were identified by physical and spectroscopic data as reported below, compared and contrasted with authentic samples.#10;Spectral data for selected products#10;6-Bromo-1,3-benzothiazol-2-amine (2e) Yellow solid; Yield = 93 percent; m.p. =202–204°C; (m.p. = 203°C), FT-IR (KBr)/t(cm-1): 3315, 3012, 2835,1580, 1476, 1261, 920, 742, 512. 1H NMR (400 MHz, CDCl3)/d ppm: 5.44 (s, 2H, NH2) 7.4–7.5 (d, 2H, Ar–H), 7.71 (s, 1H, Ar–H); 13C NMR/(100 MHz, DMSO-d6)/d ppm: 119, 120.9, 125.15, 126.07, 133.1, 152.15, 167.75.#10;
References: [1] Synlett, 2012, vol. 23, # 15, p. 2219 - 2222.
[2] Research on Chemical Intermediates, 2016, vol. 42, # 12, p. 7855 - 7868.
  • 4
  • [ 333-20-0 ]
  • [ 95-76-1 ]
  • [ 24072-75-1 ]
YieldReaction ConditionsOperation in experiment
19% at 0 - 15℃; for 16 h; j00320j To a mixture of 3,4-dichloroaniline (10 g, 62 mmol) and potassium thiocyanate (48 g, 0.49 mol) in acetic acid (160 mL) at 0 °C was added slowly with constant stirring a solution of liquidbromine (31 g, 0.19 mol) in acetic acid (160 mL). The temperature was maintained at 0 °C throughout the addition. The solution was stirred for 2 hours at 0°C and 14 hours at 15 °C, then diluted with water (100 mL), adjusted to pH 78 with ammonium hydroxide and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with brine (3 x 300 mL) and concentrated in vacuo. The residue was purified by prep-HPLC [Instmment: GX-B; Column: GEMNI 250 x 50 mm, particle size: 10 .im; Mobile phase: 25-50percent acetonitrile in H20 (add 0.1percent TFA, v/v)j to give compound B- 24 (2.6 g, 19percent yield) as a white solid. LCMS (J): tR=0.694 mi (ES) m/z (M+H)219.0. ‘H-NMR (CD3OD, 400 MHz): 7.89 (s, 1H), 7.55 (s, 1H).
References: [1] Patent: WO2017/69980, 2017, A1, . Location in patent: Paragraph 00319; 00320.
[2] Bioorganic Chemistry, 2016, vol. 67, p. 130 - 138.
  • 5
  • [ 333-20-0 ]
  • [ 95-76-1 ]
  • [ 24072-75-1 ]
  • [ 25150-27-0 ]
References: [1] Journal of Heterocyclic Chemistry, 1971, vol. 8, p. 309 - 310.
  • 6
  • [ 349403-39-0 ]
  • [ 333-20-0 ]
  • [ 4299-07-4 ]
References: [1] Journal of Organic Chemistry, 2012, vol. 77, # 8, p. 4148 - 4151.
  • 7
  • [ 1824-81-3 ]
  • [ 333-20-0 ]
  • [ 98-88-4 ]
  • [ 96938-51-1 ]
References: [1] Dalton Transactions, 2014, vol. 43, # 21, p. 7945 - 7957.
 

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