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[ CAS No. 68283-19-2 ] {[proInfo.proName]}

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Chemical Structure| 68283-19-2
Chemical Structure| 68283-19-2
Structure of 68283-19-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 68283-19-2 ]

CAS No. :68283-19-2 MDL No. :MFCD00239516
Formula : C8H14N2O Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 154.21 Pubchem ID :-
Synonyms :

Safety of [ 68283-19-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 68283-19-2 ]

* 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 [ 68283-19-2 ]

[ 68283-19-2 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 96-26-4 ]
  • [ 18257-46-0 ]
  • [ 68283-19-2 ]
  • 2
  • [ 68283-19-2 ]
  • [ 79047-41-9 ]
YieldReaction ConditionsOperation in experiment
With N-chloro-succinimide
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran; acetonitrile / 2 h / 0 °C 2: 1.) NCS, 2.) Zn, AcOH / 1.) THF, acetonitrile, from -5 deg C to 0 deg C, 0.75 h, 2.) frp, -5 deg C to 0 deg C, 1.5 h
With N-chloro-succinimide In water; ethyl acetate R.3 <Production of 2-butyl-4-chloro-5-hydroxymethylimidazole> Reference Example 3 To 210 g of ethyl acetate were added 15.4 g of 2-butyl-5-hydroxymethylimidazole and 14.7 g of N-chlorosuccinimide and the reaction was carried out with stirring at 20° C. for 3 hours. The reaction mixture was then concentrated under reduced pressure to remove 120 g of ethyl acetate. The crystals obtained by filtration were rinsed with 100 ml of water and dried to give 11.9 g of crystals. Quantitative analysis of this crystalline product by HPLC revealed that it contained 2.5% of 2-butyl-4,5-dichloroimidazole.
  • 3
  • [ 50790-93-7 ]
  • [ 50-00-0 ]
  • [ 68283-19-2 ]
  • [ 136317-69-6 ]
  • 4
  • [ 540-67-0 ]
  • [ 68283-19-2 ]
  • [ 79047-41-9 ]
YieldReaction ConditionsOperation in experiment
16 g (52%) With N-chloro-succinimide In tetrahydrofuran; diethyl ether 2.i (i) (i) 2-n-butyl-4-chloro-5-hydroxymethylimidazole To a solution of 2-n-butyl-5-hydroxymethylimidazole (25 g, 0.162 mol, prepared in Example 1 (i)) in 250 ml of tetrahydrofuran and 250 ml of 2-methoxyethane under argon was added portionwise N-chlorosuccinimide (26 g, 0.195 mol). The reaction mixture was heated at 50°-55° C. for 2 hours. The solvents were removed in vacuo and the residue for 48 hours. The solid was filtered and then stirred with 100 ml of diethyl ether for 1 hour. The solid was collected to give 16 g (52%) of 2-n-butyl-4-chloro-5-hydroxymethylimidazole.
  • 5
  • [ 109-86-4 ]
  • [ 68283-19-2 ]
  • [ 79047-41-9 ]
YieldReaction ConditionsOperation in experiment
With N-chloro-succinimide In 1,4-dioxane; water; ethyl acetate R.12 REFERENCE EXAMPLE 12 REFERENCE EXAMPLE 12 In a mixture of 70 ml of dioxane and 60 ml of methyl cellosolve was dissolved 4 g of 2-butyl-5-hydroxymethylimidazole, and 3.9 g of N-chlorosuccinimide was added to the solution, followed by stirring at 40° C. for 1 hour. The reaction solution was evaporated to dryness under reduced pressure, and 100 ml each of water and ethyl acetate were added to the residue to shake for mixing. The ethyl acetate layer was evaporated to dryness under reduced pressure, and the residue was dissolved in 50 ml of ether. The solution was allowed to cool, thereby yielding 2.4 g of 2-butyl-4-chloro-5-hydroxymethylimidazole deposited as colorless prisms, m.p. 147°-148° C. Elementary analysis, for C8 H13 N2 OCl
  • 6
  • [ 96-26-4 ]
  • [ 57246-71-6 ]
  • [ 68283-19-2 ]
YieldReaction ConditionsOperation in experiment
48% With ammonia; In water; isopropyl alcohol; at 0 - 70℃; under 9562.44 - 11769.2 Torr; for 11.5h; Comparative Example 1; a. Preparation of 2-butyl-4-hydroxymethylimidazole (BHI) 140 g (1.15 mol) methyl pentanimidate prepared according to the method of example 1, 95% purity and 84 g (0.93 mol) 1,3-<strong>[96-26-4]dihydroxyacetone</strong> were charged in 47 ml of isopropyl alcohol and cooled to 0-5 C. Ammonia gas was passed through at a pressure of 13-16 kg/cm2 at a temperature of 65-70 C. while stirring for 6 hrs. The reaction mixture was cooled to room temperature and the ammonia pressure was released. The reaction mixture was then subsequently heated to 55-60 C., transferred to 350 ml of deionised water, stirred for 30 min, and cooled to 0-5 C. The cold mixture was stirred for another 5 hrs at 0-5 C., filtered and washed with 25 ml of deionised water. Crude material was recrystallized by dissolution into 100 ml of acetonitrile at 65-70 C. The clear solution was then cooled to 0-5 C. and stirred for another 2 hrs. Finally, the solid material was filtered off, washed with 12.5 ml of acetonitrile and dried under vacuum at 30-40 C. for 6-8 hrs. The yield of 2-butyl-4-hydroxymethylimidazole obtained was 87 g (0.55 mol; 48%) with a purity of 97% by HPLC.
  • 7
  • [ 114772-40-6 ]
  • [ 68283-19-2 ]
  • 4'-(2-butyl-4-hydroxymethylimidazol-1-ylmethyl)biphenyl-2-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 12h;Inert atmosphere; The same procedure as above using (2-butyl-1Himidazol-4-yl)methanol 7b (1.225 g, 7.95 mmol), anhydrous DMF (8 mL), 1 (1.378 g, 3.97 mmol), and K2CO3 (1.10 g,7.95 mmol) afforded a residue which was purified by column chromatography (eluent: CH2Cl2/MeOH, 98:2) to give a white solid (940 mg, 2.23 mmol, 56% yield). M.p. 118-121C. 1H NMR (400 MHz, DMSO-d6): delta 0.86 (t, J = 7.3 Hz, 3H, CH3), 1.20 (s, 9 H, tBu), 1.27-1.37 (m, 2 H, CH2), 1.54-1.62 (m, 2 H, CH2), 2.54-2.58 (m, 2 H, CH2), 4.30 (d, J = 5.5Hz, 2 H, CH2OH), 4.78 (t, J = 5.5 Hz, 1 H, OH), 5.17 (s, 2H, CH2N), 6.95 (s, 1 H, imidazole), 7.19 (d, J = 8.3 Hz, 2 H,Harom), 7.27 (d, J = 8.3 Hz, 2 H, Harom), 7.35 (dd, J = 1.1, 7.6Hz, 1 H, Harom), 7.46 (dt, J = 1.3, 7.6 Hz, 1 H, Harom), 7.57(dt, J = 1.5, 7.6 Hz, 1 H, Harom), 7.68 (dd, J = 1.3, 7.6 Hz,1 H, Harom). ESI-HRMS m/z: calcd for C26H32N2O3([M+H]+): 421.2486; found: 421.2495.
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