Triethylamine → HCID 12760483, compound

HRID 1578152Notes

Reaction equation

HRID 1578152 reaction equation
[CH2:1]([NH: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][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(N(CC)CC)C.[Cl:41][CH:42]([Cl:54])[C:43]1[CH:53]=[CH:52][C:46]([O:47][CH2:48][C:49](Cl)=[O:50])=[CH:45][CH:44]=1>C(Cl)Cl>[CH2:18]([N:17]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:49](=[O:50])[CH2:48][O:47][C:46]1[CH:52]=[CH:53][C:43]([CH:42]([Cl:54])[Cl:41])=[CH:44][CH:45]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85571N-Hexadecyl-1-hexadecanamineHCID 12760482HCID 12760482, compound

Product 1

HCID 12760483HCID 12760483, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dihexadecylamine (8.88 g, 0.019 mole) was dissolved in a solution of methylene chloride (75 ml) and triethylamine (2.02 g, 0.020 mole). 4-Dichloromethylphenoxy acetyl chloride (3.97 g, 0.02 mole), dissolved in methylene chloride (25 ml), was then added dropwise over a period of 10 minutes, and the resulting clear solution was stirred for 16 hours. The reaction mixture was then washed with water (2×100 ml), saturated sodium bicarbonate solution (2×100 ml) and saturated sodium chloride solution (2×100 ml), dried over sodium sulfate, filtered, and concentrated under vacuum to the desired amide: oil, 10.83 g (92% yield).

Workup

  1. additionwas then added dropwise over a period of 10 minutes
  2. washThe reaction mixture was then washed with water (2×100 ml), saturated sodium bicarbonate solution (2×100 ml) and saturated sodium chloride solution (2×100 ml)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum to the desired amide

Sources & evidence

ORD record
ord-fd12d533e38747f9b2465be088169c57
Source dataset
uspto-grants-1981_09
Patent number
US04291060

Reaction notes

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