Water → HCID 22132160, compound

HRID 1856621Notes

Reaction equation

HRID 1856621 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:8][C:9]1[CH:10]=[CH:11][C:12]2[C:21]([CH:22]=1)=[N:20][C:19]1[C:14](=[CH:15][CH:16]=[C:17]([NH2:23])[CH:18]=1)[CH:13]=2.[CH2:24](Br)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43].O>CN1C(=O)N(C)CC1>[CH2:24]([NH:23][C:17]1[CH:16]=[CH:15][C:14]2[C:19]([CH:18]=1)=[N:20][C:21]1[C:12](=[CH:11][CH:10]=[C:9]([NH:8][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH3:24])[CH:22]=1)[CH:13]=2)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 202711-BromoeicosaneHCID 197873Proflavin hydrochloride

Product 1

HCID 22132160HCID 22132160, compound

Reagents, catalysts & solvents 1

HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Conditions

Temperature
50 °C

Procedure

2.53 g of anhydrous potassium carbonate are added to a solution of 2.5 g of 3,6-diaminoacridine hydrochloride and 2.95 g of 1-eicosyl bromide in 20 ml of N,N'-dimethylethyleneurea, and the mixture is stirred at 50° C. for 86 hours. The cooled reaction mixture is subsequently poured into water, and the orange-brown suspension is extracted with methylene chloride. The organic phase is washed with water and dried over sodium sulfate. After evaporation, 2N HCl is added to the brown oil. The red precipitate formed is filtered off, washed with water and then dried in a high vacuum. The resultant red-brown crystals are taken up in methylene chloride/methanol (10:1) and chromatographed on silica gel. After evaporation, the residue is taken up in diethyl ether/methanol (10:1) and re-chromatographed on silica gel, giving the title compound as red crystals, absorption spectrum (ethanol): λmax =472 nm; ε=42 200.

Workup

  1. customThe cooled reaction mixture
  2. extractionthe orange-brown suspension is extracted with methylene chloride
  3. washThe organic phase is washed with water
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporation, 2N HCl
  6. additionis added to the brown oil
  7. customThe red precipitate formed
  8. filtrationis filtered off
  9. washwashed with water
  10. customdried in a high vacuum
  11. customchromatographed on silica gel
  12. customAfter evaporation
  13. customre-chromatographed on silica gel
  14. customgiving
  15. customthe title compound as red crystals, absorption spectrum (ethanol)

Sources & evidence

ORD record
ord-aa35b3dd034a42fab15a0069bec14d52
Source dataset
uspto-grants-2000_11
Patent number
US06143570

Reaction notes

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