Ethanolamine → 4-(2-Aminoethyloxy)-2-hexadecylcarbamoyl-1-naphthol p-toluenesulfonate

HRID 463298Notes

Reaction equation

HRID 463298 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][C:3]=1[C:13](=[O:31])[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].[C:32]1([CH3:42])[CH:37]=[CH:36][C:35]([S:38]([OH:41])(=[O:40])=O)=[CH:34][CH:33]=1.[CH2:43]([CH2:45][NH2:46])O.C1(C)C=CC=CC=1>O>[C:32]1([CH3:42])[CH:33]=[CH:34][C:35]([S:38]([O:1][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([O:12][CH2:43][CH2:45][NH2:46])=[CH:4][C:3]=2[C:13](=[O:31])[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])(=[O:40])=[O:41])=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 30891342-Naphthalenecarboxamide, N-hexadecyl-1,4-dihydroxy-

Product 1

HCID 572528864-(2-Aminoethyloxy)-2-hexadecylcarbamoyl-1-naphthol p-toluenesulfonateYield 52.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 128 g of 1,4-dihydroxy-2-hexadecylcarbamoylnaphthalene, 285 g of p-toluenesulfonic acid and 73 g of ethanolamine was added 300 ml of toluene. The resulting mixture was heated under reflux for about 2 hours under nitrogen atmosphere, during which water was removed by a water separator. Toluene was then evaporated off under reduced pressure and 1.5 l of water was added into the residue. Precipitated crystals were collected and recrystallized from ethyl acetate to give 99 g of 4-(2-aminoethyloxy)-2-hexadecylcarbamoyl-1-naphthol p-toluenesulfonate. Yield: 51%. M.P.: 140°-146° C.

Workup

  1. temperatureThe resulting mixture was heated
  2. customwas removed by a water separator
  3. customToluene was then evaporated off under reduced pressure and 1.5 l of water
  4. additionwas added into the residue
  5. customPrecipitated crystals
  6. customwere collected
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-8bd5d25b8a4c46e9a93b97c778b55422
Source dataset
uspto-grants-1985_05
Patent number
US04518682

Reaction notes

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