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[ CAS No. 20485-44-3 ] {[proInfo.proName]}

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Chemical Structure| 20485-44-3
Chemical Structure| 20485-44-3
Structure of 20485-44-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 20485-44-3 ]

CAS No. :20485-44-3 MDL No. :MFCD00081191
Formula : C6H16N2 Boiling Point : -
Linear Structure Formula :((CH3)2CNH2)2 InChI Key :-
M.W : 116.20 Pubchem ID :-
Synonyms :

Safety of [ 20485-44-3 ]

Signal Word:Danger Class:8,3
Precautionary Statements:P210-P235-P240-P241-P242-P243-P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P321-P363-P370+P378-P403+P235-P405-P501 UN#:2734
Hazard Statements:H225-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 20485-44-3 ]

* 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 [ 20485-44-3 ]
  • Downstream synthetic route of [ 20485-44-3 ]

[ 20485-44-3 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 20485-44-3 ]
  • [ 70298-88-3 ]
  • [ 5029-67-4 ]
  • [ 113975-32-9 ]
YieldReaction ConditionsOperation in experiment
23% With n-butyllithium; iodine In tetrahydrofuran EXAMPLE 10
Compounds of the following general formula II-10 may be made, for example by the following general scheme.
Iodopyridine 16.
The 3-(Pivaloylamino)pyridine 15 (1.9 g, 11 mmol) and tetramethylethylene-diamine (4.0 mL, 26 mmol) were dissolved in dry THF (60 mL) and cooled to -78° C.
While maintaining the temperature between -78° C. and -65° C., nBuLi (2.5 M solution in hexanes, 10.6 mL, 26.5 mmol) was added dropwise.
The reaction was allowed to warm to -10° C. for 2 h, and then cooled back down to -78° C. Iodine (6.73 g, 26.5 mmol) dissolved in dry THF (20 mL) was added slowly.
After stirring for 2 h at -78° C., the reaction was quenched with ice.
Excess iodine was destroyed with addition of saturated potassium thiosulfate solution.
The product was extracted with CH2Cl2, and the organic layers were washed with brine.
The mixture was concentrated in vacuo to a black oil which was chromatographed (1:1 EtOAc/Hexanes; 2:1 EtOAc/Hexanes) to give 700 mg (23percent) of 2,2-dimethyl-N-(4-iodo-3-pyridinyl)propanamide as a yellow solid. 1H-NMR (DMSO-d6 300 MHz) δ 9.24 (s, 1H), 8.35 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 1.26 (s, 9H). MS (ES+)=305.
Reference: [1] Patent: US2003/22883, 2003, A1,
  • 2
  • [ 20485-44-3 ]
  • [ 63675-72-9 ]
YieldReaction ConditionsOperation in experiment
30% With n-butyllithium; ammonium chloride In tetrahydrofuran; methanol; hexane; dichloromethane EXAMPLE 5
Isobutyl methyl (-)-1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-pyridine-3,5-dicarboxylate STR10
After addition of 20 ml of tetramethylethylenediamine, 20 ml (32 mmol) of a 1.6 molar solution of butyl-lithium in n-hexane were added dropwise to a solution of 7.1 g (31 mmol) of methyl (S)-3-[(2-methoxymethylpyrrolidin-1-yl)-imino]-butyrate in 60 ml of absolute tetrahydrofuran at -70° C. under nitrogen.
A solution of 9 g (31 mmol) of isobutyl 2-(2-nitrobenzylidene)-acetoacetate in 50 ml of tetrahydrofuran was then added dropwise at -70° C., and the solution was stirred for a further hour at -70° C.
The cooling bath was removed and, after the solution had reached room temperature (about 3 to 4 hours), it was slowly poured into ether/water.
The aqueous phase was extracted again with ether and the combined organic extracts were dried over anhydrous sodium sulphate.
Removal of the solvent by distillation in vacuo gave an oily intermediate (12.8 g, M =/519), which was purified by chromatography over silica gel.
6.4 g (12.3 mmol) of this compound were dissolved in 25 ml of methanol and, after addition of 1.61 g (30.2 mmol) of ammonium chloride, the mixture was heated under reflux for 15 hours.
The solvent was distilled off in vacuo, the residue was taken up in methylene chloride and the mixture was washed with water.
The organic phase was dried over anhydrous sodium sulphate and concentrated in vacuo and the oily residue was purified by chromatography to give 1.4 g (30percent) of an amorphous product.
[α]D20 =-166.4° (0.49percent w/v, ethanol).
Reference: [1] Patent: US4703119, 1987, A,
  • 3
  • [ 20485-44-3 ]
  • [ 67-72-1 ]
  • [ 455-38-9 ]
  • [ 102940-86-3 ]
Reference: [1] Patent: US5334753, 1994, A,
  • 4
  • [ 496-16-2 ]
  • [ 20485-44-3 ]
  • [ 196799-45-8 ]
YieldReaction ConditionsOperation in experiment
35% With n-butyllithium In <i>N</i>-methyl-acetamide; hexane; water; ethyl acetate; Petroleum ether (1)
7-Formyl-2,3-dihydrobenzofuran
108 ml of an n-butyllithium solution (2.1M) in hexane and 26.7 g (230 mmol) of tetramethylethylenediamine (TMEDA) are introduced into a 1 liter round-bottomed flask.
The mixture is stirred at room temperature for 15 minutes and 23 g (190 mmol) of 2,3-dihydrobenzofuran are added.
The mixture is stirred for 4 hours at 35° C., cooled to -78° C. and 13.9 g (190 mmol) of dimethylformamide are added.
The temperature is allowed to return to 20° C., 500 ml of water are added and extraction is carried out with ethyl acetate (3*200 ml).
The organic phases are combined, dried and concentrated under vacuum.
The residue is purified by silica flash chromatography (elution: 5percent ethyl acetate in petroleum ether).
9.85 g (Yield: 35percent) of 7-formyl-2,3-dihydrobenzofuran are obtained--M.p.: 55° C.
Reference: [1] Patent: US6063810, 2000, A,
  • 5
  • [ 1634-04-4 ]
  • [ 20485-44-3 ]
  • [ 79427-88-6 ]
YieldReaction ConditionsOperation in experiment
52.5% With hydrogenchloride; n-butyllithium; acetic acid In tetrahydrofuran; hexane; water EXAMPLE 5
Preparation of 2-hydroxy-5-(trifluoromethyl)benzoic acid (R =H, X =COOH, Y =H)
2.9 g (25 mmol) of tetramethylethylenediamine and 15.9 ml (15percent strength, 26 mmol) of butyllithium in hexane are introduced at -20° C. and 5 g (HPLC: 98percent, 19.9 mmol) of 4-(trifluoromethyl)phenyl 2-tetrahydropyranyl ether dissolved in 10 ml of THF are added dropwise.
After 30 minutes, carbon dioxide dried by means of a phosphorus pentoxide cartridge is introduced for 30 min.
The reaction mixture is allowed to warm to 20° C. overnight, 5 ml of water, 8 ml of conc. hydrochloric acid and 10 ml of methyl t-butyl ether are added and a colorless solid (0.4 g, 4-hydroxybenzotrifluoride-3,5-dicarboxylic acid) is filtered off with suction, the phases are separated, the organic phase is washed once with saturated sodium chloride solution and the combined aqueous phases are washed three times with 5 ml of methyl t-butyl ether each time.
The organic phases are combined, dried over sodium sulfate and concentrated in vacuo.
The residue is purified by column chromatography (silica gel, petroleum ether/methyl t-butyl ether =95:5, +0.1 ml of AcOH/100 ml of eluent) and extraction under basic conditions with methyl t-butyl ether and under acidic conditions with dichloromethane. 2.2 g (HPLC: 97.8percent, 14.5 mmol, yield 52.5percent) of 2-hydroxy-5-(trifluoromethyl)benzoic acid are obtained in the form of a colorless solid. (M.p.: 149 to 151° C.).
Reference: [1] Patent: US2004/92754, 2004, A1,
  • 6
  • [ 109-72-8 ]
  • [ 20485-44-3 ]
  • [ 56700-70-0 ]
  • [ 154048-89-2 ]
Reference: [1] Patent: US2003/78277, 2003, A1,
  • 7
  • [ 23145-05-3 ]
  • [ 227802-36-0 ]
  • [ 5419-55-6 ]
  • [ 20485-44-3 ]
  • [ 223576-64-5 ]
YieldReaction ConditionsOperation in experiment
73% With hydrogenchloride; n-butyllithium In PPA; hexane Step A:
5-Chlorobenzofuran-2-boronic acid
5-Chlorobenzofuran was prepared by heating 4-chlorophenoxyacetaldehyde dimethylacetal in polyphosphoric acid; yield: 73percent.
To a solution of 8.8 g (57.7 mmol) 5-chlorobenzofuran in 250 ml dry ether were added 7.32 g (63.0 mmol) tetramethylethylenediamine (TMEDA).
The solution was kept below -60° C. under argon, while 37.5 ml of a 1.6M solution of butyllithium in hexane was added dropwise.
It was warmed to -10° C. during 45 min and stirred at this temperature for another 30 min.
The mixture was cooled again below -60° C. followed by dropwise addition of 35.7 g (190 mmol) triisopropyl borate.
After warming to room temperature the mixture was quenched with 70 ml 2N hydrochloric acid and stirred for 1 h.
The organic layer was washed three times with 30 ml 2N hydrochloric acid, twice with water, and extracted with 2N sodium hydroxide solution, successively.
The alkaline aqueous layer was brought to pH5 and extracted with tert.-butylmethylether.
All organic layers were combined, dried over sodium sulfate, and concentrated in vacuo to give the pale yellow crystalline boronic acid which was used for the next step without further purification.
yield: 9.4 g (83percent); MS 196 (M+).
Reference: [1] Patent: US6410562, 2002, B1,
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