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Chemical Structure| 112193-77-8 Chemical Structure| 112193-77-8

Structure of 112193-77-8

Chemical Structure| 112193-77-8

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Product Details of [ 112193-77-8 ]

CAS No. :112193-77-8
Formula : C8H24N4O8S2
M.W : 368.43
SMILES Code : O=S(O)(O)=O.O=S(O)(O)=O.N1CCNCCNCCNCC1

Safety of [ 112193-77-8 ]

Application In Synthesis of [ 112193-77-8 ]

* 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 [ 112193-77-8 ]

[ 112193-77-8 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 57280-22-5 ]
  • [ 497-19-8 ]
  • [ 112193-77-8 ]
  • [ 138168-36-2 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; chloroacetic acid; In methanol; ethanol; water; butan-1-ol; Example 2a 10-(1-Hydroxymethyl-2,3-dihydroxypropyl)-1,4,7-triscarboxymethyl-1,4,7,10-tetraazacyclododecane 68 g (1.7 mol) of sodium hydroxide is added to 141.1 g (250 mmol) of 1,4,7,10-tetraazacyclododecanetetrasulfate in 600 ml of n-butanol. The mixture is heated and water is azeotropically distilled off. Then, 55.0 g (382 mmol) of 4,4-dimethyl-3,5,8-trioxabicyclo-[5,1,0]-octane is instilled. After completion of the addition, it is refluxed for one hour. Then, it is cooled to room temperature, mixed with 500 ml of water and stirred for 30 minutes. The phases are separated and the butanol phase is evaporated to dryness. The residue is taken up in 600 ml of water and extracted three times with ethyl acetate. The water phase is mixed with 95 g of chloroacetic acid and brought to pH 10. After adding 159 g of Na2 CO3, it is heated to 80 C. and stirred for four hours. Then, 20 g of chloroacetic acid is added, and it is stirred for another twelve hours at 80 C. The reaction mixture is cooled to room temperature, adjusted to pH 0.8 with concentrated hydrochloric acid, heated to 60 C. and stirred for one more hour. Then, it is evaporated to dryness, mixed with 400 ml of a mixture of methanol/ethanol 1:1 and again concentrated by evaporation. This process is repeated, the residue is taken up in 1000 ml of methanol, stirred for 90 minutes at 50 C. and cooled to 0 C. The precipitating potassium chloride is suctioned off and washed twice with methanol. The combined filtrates are evaporated to dryness in a vacuum. The yield of crude product is 176 g. It is now dissolved in 200 ml of deionized water and added on a column with 2.7 l of Amberlite AMB 252c. The column is washed with deionized water until conductivity is no longer to be detected in the elude. Then, the product is eluted with water/ammonia. The substance-containing fractions are combined and evaporated to dryness. 105 g (93% of theory) of 10-(1-hydroxymethyl-2,3-dihydroxy-propyl)-1,4,7-triscarboxymethyl-1,4,7,10-tetraazacyclododecane is obtained. Elementary analysis: Cld: C 47.98 H 7.61 N 12.43 (corrected for water) Fnd: C 47.15 H 7.72 N 12.39 Water content: 9.5%
  • 2
  • [ 57280-22-5 ]
  • [ 112193-77-8 ]
  • 3-(1,4,7,10-tetraazacyclododecan-1-yl)butane-1,2,4-trioldihydrochloride [ No CAS ]
  • 10-(1-Hydroxymethyl-2,3-dihydroxypropyl-1,4,7,10-tetraazacyclododecane tetrahydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium hydroxide; In methanol; water; butan-1-ol; Example 1a 10-(1-Hydroxymethyl-2,3-dihydroxypropyl-1,4,7,10-tetraazacyclododecane tetrahydrochloride 120 g (3 mol) of sodium hydroxide is added under nitrogen atmosphere to 282.3 g (500 mmol) of 1,4,7,10-tetraazacyclododecanetetrasulfate in 1200 ml of n-butanol. The mixture is heated and resulting water is azeotropically distilled off. Then, 86.5 g (600 mmol) of <strong>[57280-22-5]4,4-dimethyl-3,5,8-trioxabicyclo[5,1,0]-octane</strong> in 200 ml of butanol is instilled. The reaction solution is refluxed for two hours and mixed again with 21.6 g (150 mmol) of <strong>[57280-22-5]4,4-dimethyl-3,5,8-trioxabicyclo[5,1,0]-octane</strong>. After another two hours of reflux, it is cooled to room temperature. The reaction mixture is mixed with 1000 ml of water and stirred for 30 minutes. The phases are separated. The butanol phase is mixed with 250 ml of concentrated hydrochloric acid, stirred for one hour at 70 C. and concentrated by evaporation in a vacuum to 200 ml. 1000 ml of absolute methanol is added. After concentration by evaporation, 500 ml of absolute methanol is again added. The solution is cooled in ice/water, and the precipitating crystals are suctioned off. The crystals are washed once with butanol and twice with methyltert-butyl ether (MTB ether) and dried. The product loses HCl with drying. 200.5 g (95% of theory) of 10-(1-hydroxymethyl-2,3-dihydroxypropyl)-1,4,7,10-tetraazacyclododecane tetrahydrochloride is obtained as white crystals. Melting point: 214-216 C. Elementary analysis: Cld: C 34.13 H 7.64 N 13.27 Cl 33.59 Fnd: C 35.19 H 7.85 N 13.67 Cl 29.61
 

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