2-(Dimethylamino)ethanol → 10-[4-[[4-(dodecyl)phenyl]azo]phenoxy]-N-(2-hydroxyethyl)-N,N-dimethyl-1-decanaminium bromide

HRID 1655708

Reaction equation

HRID 1655708 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]=[N:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[CH:23][CH:22]=2)=[CH:15][CH:14]=1.[CH3:39][N:40]([CH3:44])[CH2:41][CH2:42][OH:43].O1CCCC1>CO>[Br-:1].[CH2:27]([C:24]1[CH:25]=[CH:26][C:21]([N:20]=[N:19][C:16]2[CH:17]=[CH:18][C:13]([O:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N+:40]([CH2:41][CH2:42][OH:43])([CH3:44])[CH3:39])=[CH:14][CH:15]=2)=[CH:22][CH:23]=1)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Participants

5

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 8028TetrahydrofuranHCID 197929294-(10-Bromodecyloxy)-4'-dodecylazobenzene

Product 1

HCID 1979292710-[4-[[4-(dodecyl)phenyl]azo]phenoxy]-N-(2-hydroxyethyl)-N,N-dimethyl-1-decanaminium bromide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 3000 ml three-necked round bottom flask was equipped with magnetic stirring, a heating mantle, a reflux condenser, and a nitrogen atmosphere. The flask was charged with 4-(10-bromodecyloxy)-4'-dodecylazobenzene (40 g, 0.068 mol), dimethylethanolamine (95.2 g, 1.068 mole) and 1050 ml of tetrahydrofuran. The reaction mixture was allowed to reflux for 24 hours. During the course of the reaction mixture. After 24 hours, the reaction mixture was cooled to room temperature, and then chilled in an ice-water bath. The crystalline solid was isolated by suction filtration. The crude product was dissolved in hot methanol and filtered to remove insoluble impurities. The methanol was removed by evaporation at reduced pressure. The crude product was recrystallized from tetrahydrofuran. Yield 28.0 g, 61.0%.

Workup

  1. customA 3000 ml three-necked round bottom flask was equipped with magnetic stirring
  2. temperatureto reflux for 24 hours
  3. temperaturechilled in an ice-water bath
  4. customThe crystalline solid was isolated by suction filtration
  5. filtrationfiltered
  6. customto remove insoluble impurities
  7. customThe methanol was removed by evaporation at reduced pressure
  8. customThe crude product was recrystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-97af92fe44694a3ca1ff6363ac04f840
Source dataset
uspto-grants-1993_10
Patent number
US05251197

Linked notes

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