Ethanol → HCID 18705592, compound

HRID 2287801Notes

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]1

Participants

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 C1,H27N5 : 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-df82ddd28f4742f8afd76fab16d03c0d
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06084093

Reaction notes

Loading…