Diisopropylethylamine → 2,7-Bis(azocan-1-ylsulfonyl)anthracene-9,10-dione

HRID 61971Notes

Reaction equation

HRID 61971 reaction equation
[CH:1]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([S:16](Cl)(=[O:18])=[O:17])[CH:11]=3)[C:6](=[O:20])[C:5]=2[CH:4]=[CH:3][C:2]=1[S:21](Cl)(=[O:23])=[O:22].C([N:28]([CH:31]([CH3:33])C)[CH2:29][CH3:30])(C)C>C(Cl)Cl>[N:28]1([S:21]([C:2]2[CH:3]=[CH:4][C:5]3[C:6](=[O:20])[C:7]4[C:12](=[CH:11][C:10]([S:16]([N:28]5[CH2:29][CH2:30][CH2:5][CH2:4][CH2:3][CH2:33][CH2:31]5)(=[O:18])=[O:17])=[CH:9][CH:8]=4)[C:13](=[O:15])[C:14]=3[CH:1]=2)(=[O:23])=[O:22])[CH2:31][CH2:33][CH2:14][CH2:1][CH2:2][CH2:30][CH2:29]1

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 234366039,10-Dioxo-9,10-dihydro-anthracene-2,7-disulfonyl dichloride

Product 1

HCID 468513512,7-Bis(azocan-1-ylsulfonyl)anthracene-9,10-dioneYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-50 °C

Procedure

Anthraquinone-2,7-disulfonylchloride (1215 mg, 3 mmole) was dissolved in 100 mL DCM. The solution was cooled to −50° C. To this solution was added 1 mL (8 mmole) of heptamethyleneimine, followed by 1 mL of diisopropylethylamine. The reaction mixture was stirred at room temperature for 4 hrs. Solvent was evaporated and the residue was treated with 1N HCl, filtered off, washed with water and dried. Crude material was crystallized from chloroform-hexane to give 1.014 g (91%) of yellow compound 1-27. H1-NMR (CDCl3): 8.70 (2H, d, C1 and C8), 8.47 (2H, d, C4 and C5), 8.22 (2H, dd, C3 and C6), 3.22 (8H, m), 1.70 (20H, m).

Workup

  1. customSolvent was evaporated
  2. additionthe residue was treated with 1N HCl
  3. filtrationfiltered off
  4. washwashed with water
  5. customdried
  6. customCrude material was crystallized from chloroform-hexane

Sources & evidence

ORD record
ord-da534233dc754001b3cad2c5e06fde76
Source dataset
uspto-grants-2016_09
Patent number
US09446021B2

Reaction notes

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