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Chemical Structure| 3034-52-4 Chemical Structure| 3034-52-4

Structure of 3034-52-4

Chemical Structure| 3034-52-4

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Product Details of [ 3034-52-4 ]

CAS No. :3034-52-4
Formula : C3H2ClNS
M.W : 119.57
SMILES Code : C1=CN=C(Cl)S1
MDL No. :MFCD00210701
InChI Key :KLEYVGWAORGTIT-UHFFFAOYSA-N
Pubchem ID :76429

Safety of [ 3034-52-4 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H226-H302-H318
Precautionary Statements:P210-P233-P240-P241-P242-P243-P264-P270-P280-P301+P312+P330-P303+P361+P353-P305+P351+P338+P310-P370+P378-P403+P235-P501
Class:3
UN#:1993
Packing Group:

Application In Synthesis of [ 3034-52-4 ]

* 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 [ 3034-52-4 ]
  • Downstream synthetic route of [ 3034-52-4 ]

[ 3034-52-4 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 3034-52-4 ]
  • [ 109-94-4 ]
  • [ 95453-58-0 ]
YieldReaction ConditionsOperation in experiment
73%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 1 h;
Stage #2: at -78℃; for 1 h;
To a stirred solution of 2-chlorothiazole E-1 (80 g) in anhydrous THF (1000 ml.) was added n- BuLi (320 ml_, 0.8 mol) drop wise at -78 °C for one hour. Ethyl formate (74 g) was added dropwise to the solution at -78 °C, and stirred for one additional hour. Saturated NH4CI was added to the reaction mixture and stirred for 30 min, then diluted with ethyl acetate. The aqueous phase was extracted with ethyl acetate. The organic phase was washed and dried, then concentrated to give the crude product, which was purified by re-crystallized with hexane/ethyl acetate to give 2-chlorothiazole-5-carbaldehyde E-2 (72 g yield: 73 percent,); 1 H NMR (400 MHz, CDCI3): δ ppm 9.96 (s., 1 H), 8.21 (s, 1 H).
References: [1] Patent: WO2016/55431, 2016, A1, . Location in patent: Page/Page column 75.
  • 2
  • [ 3034-52-4 ]
  • [ 95453-58-0 ]
YieldReaction ConditionsOperation in experiment
62% With n-butyllithium In tetrahydrofuran; hexane; ethyl acetate; N,N-dimethyl-formamide; Petroleum ether Example 53
Preparation of 2-chlorothiazole-5-carboxaldehyde (Prepared by the Literature Procedure: I. Sawhney and J. R. H. Wilson. J. Chem. Soc. Perkin Trans I, 1990, 329-331)
To a solution of 2-chlorothiazole (see Example 51, 500 mg, 4.2 mmol) in distilled tetrahydrofuran (7 mL) at -78° C. was added n-butyllithium (2.5M solution in hexane, 4.5 mmol, 1.78 mL) slowly dropwise.
After stirring 10 min at -78° C., N,N-dimethylformamide (5.4 mmol, 0.42 mL) was added and the reaction was warmed slowly to room temperature over 2 h.
The reaction mixture was then poured slowly onto 2N hydrochloric acid solution (10 mL), stirred 5 min and then was made basic with 50percent ammonium hydroxide solution.
The water layer was extracted with dichloromethane (2*50 mL) and the combined organic layers were washed with brine (25 mL), dried (MgSO4), filtered and concentrated in vacuo.
The residue was flash chromatographed (silica gel, 20percent ethyl acetate in petroleum ether) to yield 2-chlorothiazole-5-carboxaldehyde (387 mg, 62percent yield) as a yellow solid.
References: [1] Patent: US2002/161237, 2002, A1, .
  • 3
  • [ 3034-52-4 ]
  • [ 68-12-2 ]
  • [ 95453-58-0 ]
References: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 2, p. 329 - 331.
 

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Technical Information

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