Ethanol → HCID 18705591, compound

HRID 2287797Notes

Reaction equation

HRID 2287797 reaction equation
C1(C)C=CC(S([N:10]2[CH2:24][N:23](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:22][CH2:21][CH2:20][N:19](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:18][CH2:17][N:16](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:15][CH2:14][N:13](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:12][CH2:11]2)(=O)=O)=CC=1.OS(O)(=O)=O.C(O)C>C(OCC)C>[NH:10]1[CH2:24][NH:23][CH2:22][CH2:21][CH2:20][NH:19][CH2:18][CH2:17][NH:16][CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 18705596HCID 18705596, compound

Product 1

HCID 18705591HCID 18705591, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1,4,7,10,14-penta(p-toluenesulfonyl)-1,4,7,10,14-pentaazacyclopentadecane prepared as in Example 12 A (28.5 g, 0.0279 mole) and concentrated H2SO4 (100 ml) was heated at 100° C. with stirring under a dry argon atmosphere for 72 H. To the resulting brown solution, ethanol (100 ml) was added dropwise with stirring at 0° C. followed by ethyl ether (1 l). The tan solid was filtered and washed thoroughly with ethyl ether. The solid was then dissolved in H2O (100 ml) and the resulting solution filtered and washed with ethyl ether. The pH of the solution was adjusted to 11 with 10N NaOH and the solvent was removed in vacuo. The resulting brown oily solid was extracted with hot THF (2×500 ml) and the THF extracts were filtered. The filtrates were combined and the solvent was removed in vacuo. The oily residue was dissolved in hot hexane and the insoluble impurities were removed by filtration. The solvent was removed in vacuo and the residual oil was purified by vacuum distillation to give 2.68 g (39% yield) of the product as a light yellow oil: bp 140-5° C. (0.10 mm Hg); 1H NMR (CDCl3) δ 1.51 (br s, 5 H), 1.68 (quint, J=6.1 Hz, 4 H), 2.73 (m, 20 H); Exact mass (M+H)+ : calcd., 244.2501; Found: 244.2555 (C12H30N5).

Workup

  1. stirringwith stirring at 0° C.
  2. filtrationThe tan solid was filtered
  3. washwashed thoroughly with ethyl ether
  4. dissolutionThe solid was then dissolved in H2O (100 ml)
  5. filtrationthe resulting solution filtered
  6. washwashed with ethyl ether
  7. customthe solvent was removed in vacuo
  8. extractionThe resulting brown oily solid was extracted with hot THF (2×500 ml)
  9. filtrationthe THF extracts were filtered
  10. customthe solvent was removed in vacuo
  11. dissolutionThe oily residue was dissolved in hot hexane
  12. customthe insoluble impurities were removed by filtration
  13. customThe solvent was removed in vacuo
  14. distillationthe residual oil was purified by vacuum distillation

Sources & evidence

ORD record
ord-e6863edb554c4fb18cfdf18f92f643e4
Source dataset
uspto-grants-2000_07
Patent number
US06084093

Reaction notes

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