2,4-Dichlorobenzylamine → HCID 19068309, compound

HRID 1957590Notes

Reaction equation

HRID 1957590 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5].C(N(CC)CC)C.[CH2:18](Br)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>C(Cl)(Cl)Cl>[CH2:29]([NH:5][CH2:4][C:3]1[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:2]=1[Cl:1])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH3:18]

Participants

5

Reactant 3

HCID 14852,4-DichlorobenzylamineHCID 8471TriethylamineHCID 89191-Bromododecane

Product 1

HCID 19068309HCID 19068309, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

In a 100-ml round-bottomed flask were placed 2,4-dichlorobenzylamine (3.5 g (20 mmol)), triethylamine (4.0 g (40 mmol)), and chloroform (10 ml) under nitrogen. While stirring, laurylbromide (4.9 g (20 mmol)) in chloroform (5 ml) was added dropwise at 50°-60° C. The mixture was stirred for 6 hours. The reaction mixture was cooled to room temperature and concentrated. The resultant concentrate was dissolved in ethyl acetate, washed with water, and purified via silica gel column chromatography (chloroform:methanol=10:1), thereby obtaining 2.3 g of N-lauryl-2,4-dichlorobenzylamine as pale yellow crystals (yield: 34%).

Workup

  1. customIn a 100-ml round-bottomed flask were placed
  2. stirringThe mixture was stirred for 6 hours
  3. concentrationconcentrated
  4. concentrationThe resultant concentrate
  5. dissolutionwas dissolved in ethyl acetate
  6. washwashed with water
  7. custompurified via silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-0b22087214d1444b8c78d5217d35b8cd
Source dataset
uspto-grants-1998_07
Patent number
US05786386

Reaction notes

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