Water → HCID 68006739, compound

HRID 2172406Notes

Reaction equation

HRID 2172406 reaction equation
C1(C)C=CC(S([N:10]2[CH2:32][CH2:31][N:30](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:29][CH2:28][N:27](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:26][CH2:25][N:24](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:23][CH2:22][N:21](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:20][CH2:19][CH2:18][N:17](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:16][CH2:15][N:14](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:13][CH2:12][CH2:11]2)(=O)=O)=CC=1.S(=O)(=O)(O)O.O>C(OCC)C>[NH:10]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28][NH:27][CH2:26][CH2:25][NH:24][CH2:23][CH2:22][NH:21][CH2:20][CH2:19][CH2:18][NH:17][CH2:16][CH2:15][NH:14][CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 86667390HCID 86667390, compound

Product 1

HCID 68006739HCID 68006739, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
90 °C

Procedure

63.3 g (0.045 mol) of the 1,5,8,12,15,18,21-Heptakis(p-tolylsulfonyl)-1,5,8,12,15,18,21-heptaazacyclotricosane was mixed with 300 ml of 98% sulfuric acid and 8 ml of water, and then the mixed solution was heated at a temperature of 90° C. for 3 days and then cooled. The mixed solution was added to 2000 ml of diethylether and then diethylether was subjected to decanting, and the residual was dissolved in 200 ml of water. A pH of the resultant solution was controlled to be pH 13 by using a NaOH aqueous solution, and the solution was filtered and extracted with ethanol. The ethanol used was evaporated from the extraction product and impurities were removed therefrom under vacuum conditions according to a kugelrohr distillation method to produce 8 g of 1,5,8,12,15,18,21-heptaazacyclotricosane.

Workup

  1. temperaturecooled
  2. customto decanting
  3. dissolutionthe residual was dissolved in 200 ml of water
  4. filtrationthe solution was filtered
  5. extractionextracted with ethanol
  6. customThe ethanol used was evaporated from the extraction product and impurities
  7. customwere removed
  8. distillationunder vacuum conditions according to a kugelrohr distillation method

Sources & evidence

ORD record
ord-9358e5309c4b46d6951014900ef45c7b
Source dataset
uspto-grants-2015_06
Patent number
US09054392B2

Reaction notes

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