4-(N,N-Bis(2-hydroxyethyl)amino)benzaldehyde → HCID 86633577, compound

HRID 11987Notes

Reaction equation

HRID 11987 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH2:13][CH2:14][OH:15])[C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1.[Cl-:16].[S:17]([CH2:36][CH2:37][NH:38][C:39](=[O:52])[CH2:40][N:41]1[C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=2[N+:43]([CH3:50])=[C:42]1[CH3:51])[S:18][CH2:19][CH2:20][NH:21][C:22](=[O:35])[CH2:23][N:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[N+:26]([CH3:33])=[C:25]1[CH3:34].[Cl-]>C(O)C.N1CCCCC1>[Cl-:16].[S:17]([CH2:36][CH2:37][NH:38][C:39](=[O:52])[CH2:40][N:41]1[C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=2[N+:43]([CH3:50])=[C:42]1[CH:51]=[CH:9][C:8]1[CH:7]=[CH:6][C:5]([N:4]([CH2:3][CH2:2][OH:1])[CH2:13][CH2:14][OH:15])=[CH:12][CH:11]=1)[S:18][CH2:19][CH2:20][NH:21][C:22](=[O:35])[CH2:23][N:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[N+:26]([CH3:33])=[C:25]1[CH:34]=[CH:9][C:8]1[CH:11]=[CH:12][C:5]([N:4]([CH2:13][CH2:14][OH:15])[CH2:3][CH2:2][OH:1])=[CH:6][CH:7]=1.[Cl-:16]

Participants

5

Reactant 2

HCID 128249654-(N,N-Bis(2-hydroxyethyl)amino)benzaldehydeHCID 866335761,1'-{disulfanediylbis[ethane-2,1-diylimino(2-oxoethane-2,1-diyl)]}bis(2,3-dimethyl-1H-benzimidazol-3-ium) chloride

Product 1

HCID 86633577HCID 86633577, compoundYield 163.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8082PiperidineSolvent

Procedure

To a stirring solution of 4-[bis(2-hydroxyethyl)-amino]benzaldehyde (1.7 g, 8.1 mmol) and 1,1′-{disulfanediylbis[ethane-2,1-diylimino(2-oxoethane-2,1-diyl)]}bis(2,3-dimethyl-1H-benzimidazol-3-ium) chloride (1.2 g, 2 mmol) in 35 ml of ethanol, 0.5 ml of piperidine was added as a catalyst. The reaction mixture was heated to reflux for 7 h. After cooling, the resulting orange solids were collected by filtration and then washed with dichloromethane and methanol. The drying afforded 1.6 g of a orange solid. Analyses were in accordance with the expected structure.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 7 h
  3. temperatureAfter cooling
  4. filtrationthe resulting orange solids were collected by filtration
  5. washwashed with dichloromethane and methanol

Sources & evidence

ORD record
ord-8955fbefec794c7e845c91bc66158cae
Source dataset
uspto-grants-2010_06
Patent number
US07727287B2

Reaction notes

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