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Chemical Structure| 20656-61-5 Chemical Structure| 20656-61-5

Structure of 20656-61-5

Chemical Structure| 20656-61-5

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Product Details of [ 20656-61-5 ]

CAS No. :20656-61-5
Formula : C4H5ClO3
M.W : 136.53
SMILES Code : O=C(OC)C(Cl)C=O
MDL No. :MFCD15142843

Safety of [ 20656-61-5 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301-H311-H331-H341
Precautionary Statements:P201-P202-P261-P264-P270-P271-P280-P302+P352-P304+P340-P308+P313-P310-P330-P361-P403+P233-P405-P501
Class:6.1
UN#:2811
Packing Group:

Application In Synthesis of [ 20656-61-5 ]

* 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.

  • Downstream synthetic route of [ 20656-61-5 ]

[ 20656-61-5 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 20656-61-5 ]
  • [ 17356-08-0 ]
  • [ 6633-61-0 ]
YieldReaction ConditionsOperation in experiment
44% A mixture of 2. 4g of g-2, water 20ml and 1.75g of thiourea was refluxed for 2 hours. The mixture was cooled to room temperature and 0.25g of norit was added and filtered. A solution of 2. 5N sodium hydroxide was added to the filtrate until neutral pH. The filtration yielded 1.23g (44%) of 2-aminothiazole-5-carboxylic acid methyl ester (g-3).
  • 2
  • [ 214834-18-1 ]
  • [ 20656-61-5 ]
  • [ 867066-22-6 ]
YieldReaction ConditionsOperation in experiment
In toluene; at 80 - 90℃; for 2.75h; A mixture of tertiary butyl 4-(aminocarbothioyl)tetrahydropyridne-1(2H)carboxylate 25.1 (1 g) and methyl chloro(formyl)acetate (1.3 g) in toluene (20 mL) was heated in an 80-90 C. oil bath for 1.75 hours. Another spatula full of the chloro(formyl)acetate was added and the heating continued another hour. The reaction was cooled and partitioned between saturated aqueous sodium bicarbonate and ethyl acetate. The organics were washed with water and brine. Drying and evaporation of the solvent gave an oily residue that was purified by flash chromatography eluting with 30% ethyl acetate hexane to give the thiazole 25.2 as a yellow oil (0.6 g). A solution of 25.2 (0.55 g) in methylene chloride (3 mL) was treated with trifluoroacetic acid (1 mL). After three hours, another portion of trifluoroacetic acid (1 mL) was added and stirring continued for three hours. The solvent was evaporated and the residue partitioned between water and ether. The aqueous phase was made basic with 1 N sodium hydroxide and extracted with chloroform. The chloroform solution was dried and the solvent evaporated to give 25.3 as a dark gum (0.187 g). A solution of the gum in methylene chloride (5 mL) and diisopropylethylamine (0.3 mL) was cooled in ice-water and treated with 4-biphenylsulphonyl chloride (0.21 g) in methylene chloride (2 mL). The cooling was removed and the reaction stirred one hour. A crystal of 4-dimethylaminopyridine was added and stirring was continued overnight. The solvent was evaporated and the residue partitioned between water and ethyl acetate. The organics were washed with 1 N hydrochloric acid, aqueous saturated sodium bicarbonate, and brine. The solvent was dried and evaporated to give a tan solid. The solid was purified by flash chromatography eluting with 60-80% ethyl acetate-hexane to give 25.3 as a tan powder (91 mg) with the expected m/e of 443 (M+H+). A mixture of methyl 2-[1-(1,1'-biphenyl-4-ylsulfonyl)piperidin-4-yl]-1,3-thiazole-5-carboxylate 25.3 (9 mg), 50% hydroxylamine in water (0.05 mL), and dioxane (1 mL) were cooled in ice-water. To the reaction was added 1N sodium hydroxide (0.053 mL) followed by removal of the cooling bath. After stirring overnight, the reaction was neutralized with 1 N hydrochloric acid (0.053 mL) and the solvent evaporated. The residue was purified by preparative hplc to give Example 25 as a floculant white solid (3.5 mg). 1H NMR (DMSO) δ: 2.75 (m, 2H), 2.15 (m, 2H), 2.5 (m, 2H), 3.1 (m, 1H), 3.75 (m, 2H), 7.45-7.55 (m, 3H), 7.72-7.96 (m, 6H), 8.08 (s, 1H), 11.3 (s, 1H); m/e=444 (M+H+).
 

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