Ethanol → HCID 18705592, compound
Reaction equation
[CH3:1][N:2]1[CH2:16][CH2:15][N:14](S(C2C=CC(C)=CC=2)(=O)=O)[CH2:13][CH2:12][N:11](S(C2C=CC(C)=CC=2)(=O)=O)[CH2:10][CH2:9][N:8](S(C2C=CC(C)=CC=2)(=O)=O)[CH2:7][CH2:6][N:5](S(C2C=CC(C)=CC=2)(=O)=O)[CH2:4][CH2:3]1.OS(O)(=O)=O.C(O)C>C(OCC)C>[CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:6][CH2:7][NH:8][CH2:9][CH2:10][NH:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 1-methyl-4,7,10,13-tetra(p-toluenesulfonyl)-1,4,7,10,13-pentaazacyclopentadecane prepared as in Example 15C (3.6 g, 4.3 mmol) and concentrated H2SO4 (15 ml) was heated at 100° C. with stirring under a dry argon atmosphere for 72 h. To the resulting brown solution, ethanol (30 mL) was added dropwise with stirring at 5° C. followed by ethyl ether (80 ml). The tan solid was filtered and dissolved in H2O (10 ml). The pH of the solution was adjusted to 10 with 10N NaOH and the solution was extracted with 6×CHCl3. The extracts were combined, dried (Na2SO4) and the solvent removed in vacuo. The crude solid was purified by crystallization from cold (-20° C.) CH3CN to give 0.50 g (51% yield) of the product as colorless needles: mp 71.0°-2.5° C.; 1H NMR (CDCl3) δ 1.90 (br s, 4 H), 2.22 (s, 3 H), 2.52 (m, 4 H), 2.68 (m, 12 H), 2.78 (m, 4 H); Anal. calcd. for C11H27N5 : C, 57.60; H, 11.86; N, 30.53. Found: C, 57.17; H, 12.13; N, 30.12.
Workup
- stirringwith stirring at 5° C.
- filtrationThe tan solid was filtered
- dissolutiondissolved in H2O (10 ml)
- extractionthe solution was extracted with 6×CHCl3
- dry with materialdried (Na2SO4)
- customthe solvent removed in vacuo
- customThe crude solid was purified by crystallization from cold (-20° C.) CH3CN
Sources & evidence
- ORD record
- ord-cf9c0bee1e294be18e4471f70fba8cb8
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05874421
Reaction notes
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