Ethanol → HCID 10384442, compound

HRID 363390Notes

Reaction equation

HRID 363390 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][N:20](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:19][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.[CH2:71](O)[CH3:72]>C(OCC)C>[NH:16]1[CH2:17][CH2:18][CH2:19][NH:20][CH2:21][CH2:22][NH:23][CH2:72][CH2:71][CH2:24][NH:10][CH2:11][CH2:12][NH:13][CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 18705589HCID 18705589, compound

Product 1

HCID 10384442HCID 10384442, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1,4,7,11,14-penta(p-toluenesulfonyl)-1,4,7,11,14-pentaazacyclopentadecane prepared as in Example 11C (26.3 g, 0.0258 mole) and concentrated H2SO4 (80 ml) was heated at 100° C. with stirring under a dry argon atmosphere for 72 h. To the resulting brown solution, ethanol (160 mL) was added dropwise with stirring at 0° C. followed by ethyl ether (400 ml). The resulting tan solid was filtered and dried in vacuo over P2O5. The tarry solid was then dissolved by the addition of 10N NaOH and the salts were removed by filtration. The solution was then extracted with CHCl3 (6×200 ml). The extracts were combined, dried (Na2SO4) and the solvent was removed in vacuo to give an oil which crystallized on standing. The crude product was dissolved in hexane and insoluble impurities were removed by filtration. Upon cooling to -20° C., 2.28 g (36% yield) of the product was obtained as colorless needles: mp 49°-51° C.; 1H NMR (CDCl3) δ 1.69 (m, 4 H), 1.78 (br s, 5 H), 2.76 (m, 20 H). Exact mass: (M+H)+ : calcd., 244. 2501; Found: 244.2557 (C12H30N5).

Workup

  1. stirringwith stirring at 0° C.
  2. filtrationThe resulting tan solid was filtered
  3. dry with materialdried in vacuo over P2O5
  4. dissolutionThe tarry solid was then dissolved by the addition of 10N NaOH
  5. customthe salts were removed by filtration
  6. extractionThe solution was then extracted with CHCl3 (6×200 ml)
  7. dry with materialdried (Na2SO4)
  8. customthe solvent was removed in vacuo
  9. customto give an oil which
  10. customcrystallized
  11. dissolutionThe crude product was dissolved in hexane
  12. custominsoluble impurities were removed by filtration
  13. temperatureUpon cooling to -20° C.

Sources & evidence

ORD record
ord-194786c393d94d9d88a1f37c638710e5
Source dataset
uspto-grants-1999_02
Patent number
US05874421

Reaction notes

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