Sulfuric Acid → HCID 22132166, compound

HRID 1856622Notes

Reaction equation

HRID 1856622 reaction equation
[OH-].[K+].S([N:13]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([NH:27]S(C3C=CC(C)=CC=3)(=O)=O)[CH:25]=2)[CH2:20][C:19]2[CH:18]=[CH:17][C:16]([NH2:38])=[CH:15][C:14]1=2)(C1C=CC(C)=CC=1)(=O)=O.Br[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45].S(=O)(=O)(O)O.[OH-].[Na+]>CN(C)C=O.C1(C)C=CC=CC=1.C(OCC)(=O)C.C(O)(=O)C.O>[CH2:40]([NH:38][C:16]1[CH:17]=[CH:18][C:19]2[C:14]([CH:15]=1)=[N:13][C:26]1[C:21](=[CH:22][CH:23]=[C:24]([NH:27][CH2:16][CH2:15][CH2:14][CH2:19][CH2:18][CH3:17])[CH:25]=1)[CH:20]=2)[CH2:41][CH2:42][CH2:43][CH2:44][CH3:45]

Participants

10

Reactant 5

HCID 1118Sulfuric AcidHCID 81011-BromohexaneHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 69537554HCID 69537554, compound

Product 1

HCID 22132166HCID 22132166, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 21584019Toluene ethylacetateSolvent

Conditions

Temperature
60 °C

Procedure

298 mg of ground potassium hydroxide are added to a solution of 500 mg of N,N'-bistosyl-3,6-diaminoacridine and 797 mg of 1-bromohexane in 25 ml of dimethylformamide, and the mixture is stirred at 60° C. for 22 hours. The cooled reaction mixture is subsequently poured into water and extracted with ethyl acetate, and the organic phase is separated off, washed with aqueous NaCl solution and then dried over sodium sulfate. Evaporation gives a dark-red oil, which is taken up in toluene/ethyl acetate (20:1) and chromatographed on silica gel. Evaporation of the solvent gives a yellow, viscous oil, which is dissolved in 11.5 ml of glacial acetic acid, 4.6 ml of 97% sulfuric acid are added with water cooling, and the mixture is then stirred at room temperature for 15 hours. The red reaction mixture is poured into ice water and adjusted to pH 11 by means of 30% NaOH. The mixture is extracted with ethyl acetate, and the organic phase is washed with 2N HCl and saturated aqueous NaCl solution and then dried over sodium sulfate. After evaporation, the dark-red, viscous oil is taken up in t-butyl methyl ether/methanol (5:1) and chromatographed on silica gel, giving the title compound as orange-red crystals having a melting point of >200° C. (decomposition). 1H-NMR (CDCl3): 8.1 [s, 1H, C(9)]; 7.44 [d, 2H, C(8)]; 6.93 [s, 2H, C(S)]; 6.82 [d, 2H, C(7)]; 3.20 [t, 4H, N-CH2 ]; 1.68 [m, 6H, CH3 ].

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with ethyl acetate
  3. customthe organic phase is separated off
  4. washwashed with aqueous NaCl solution
  5. dry with materialdried over sodium sulfate
  6. customEvaporation
  7. customgives a dark-red oil, which
  8. customchromatographed on silica gel
  9. customEvaporation of the solvent
  10. customgives a yellow, viscous oil, which
  11. stirringthe mixture is then stirred at room temperature for 15 hours
  12. customThe red reaction mixture
  13. extractionThe mixture is extracted with ethyl acetate
  14. washthe organic phase is washed with 2N HCl and saturated aqueous NaCl solution
  15. dry with materialdried over sodium sulfate
  16. customAfter evaporation
  17. customchromatographed on silica gel

Sources & evidence

ORD record
ord-3afd0a47049f49b6b09cfcdc92104656
Source dataset
uspto-grants-2000_11
Patent number
US06143570

Reaction notes

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