Ethanol → 1,4,7,10,13-Pentaazacyclohexadecane

HRID 1532586Notes

Reaction equation

HRID 1532586 reaction equation
C1(C)C=CC(S([N:10]2[CH2:25][CH2:24][CH2:23][N:22](S(C3C=CC(C)=CC=3)(=O)=O)[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[CH2:25][CH2:24][CH2:23][NH: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 22013689HCID 22013689, compound

Product 1

HCID 63963291,4,7,10,13-PentaazacyclohexadecaneYield 15%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1,4,7,10,13-penta(p-toluenesulfonyl)-1,4,7,10,13-pentaazacyclohexadecane prepared as in Example 1D (30 g, 0.030 mole) and concentrated H2SO4 (100 ml) was heated at 100° C. with stirring under a dry argon atmosphere for 69 h. To the resulting brown solution, ethanol (200 mL) was added dropwise with stirring at 5° C., followed by ethyl ether (500 ml). The tan solid was filtered and washed thoroughly with ethyl ether. The solid was then dissolved in H2O (75 ml), the pH was adjusted to 10 with 10N NaOH, and the solution was extracted with CHCl3 (6×200 ml). The extracts were combined and dried (Na2SO4), and the solvent was removed in vacuo. The resulting yellow solid was purified by recrystallization from hexane to give 1.0 g (15% yield) of the product as colorless needles: mp 109-110.5° C.; 1H NMR (CDCl3)δ 1.72 (quint, J=5.4 Hz, 2 H), 1.76 (br s, 5 H), 2.73 (m, 20 H); Anal. calcd. for C11H27N5: C, 57.60; H, 11.86; N, 30.53. Found: C, 57.77; H, 12.35; N, 30.57.

Workup

  1. stirringwith stirring at 5° C.
  2. filtrationThe tan solid was filtered
  3. washwashed thoroughly with ethyl ether
  4. dissolutionThe solid was then dissolved in H2O (75 ml)
  5. extractionthe solution was extracted with CHCl3 (6×200 ml)
  6. dry with materialdried (Na2SO4)
  7. customthe solvent was removed in vacuo
  8. customThe resulting yellow solid was purified by recrystallization from hexane

Sources & evidence

ORD record
ord-05e0efe5d1964e3b9ed9758d8d2c7eb3
Source dataset
uspto-grants-2001_03
Patent number
US06204259B1

Reaction notes

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