2,4-Dichlorobenzyl chloride → N,N-Dibutyl-N-[(2,4-dichlorophenyl)methyl]butan-1-aminium chloride

HRID 1154977Notes

Reaction equation

HRID 1154977 reaction equation
[CH2:1]([N:5]([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[Cl:14][C:15]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:16]=1[CH2:17]Cl>C(OCC)C>[Cl-:14].[CH2:10]([N+:5]([CH2:1][CH2:2][CH2:3][CH3:4])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:17][C:16]1[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:15]=1[Cl:14])[CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 72122,4-Dichlorobenzyl chlorideHCID 7622Tributylamine

Product 1

HCID 165101N,N-Dibutyl-N-[(2,4-dichlorophenyl)methyl]butan-1-aminium chloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Eighteen and fifty-four one-hundredths parts of tributylamine and 19.54 parts of 2,4-dichlorobenzyl chloride were placed in a 250 ml. glass stoppered flask. 70.8 parts of diethyl ether was added and the flask tightly stoppered and allowed to react at room temperature. After a considerable time an oil began to form and after 2 to 3 months, the product began to crystallize. At the end of six months, the crystals were filtered, washed with hexane and dried under vacuum. 16.7 parts of tributyl-2,4-dichlorobenzylammonium chloride was obtained, the compound having 3.33% nitrogen, the calculated value for nitrogen (for C19H32Cl3N) is 3.69%.

Workup

  1. customto react at room temperature
  2. customto form and after 2 to 3 months
  3. customto crystallize
  4. filtrationAt the end of six months, the crystals were filtered
  5. washwashed with hexane
  6. customdried under vacuum

Sources & evidence

ORD record
ord-0e323a29d35e450894cee8251a780659
Source dataset
uspto-grants-1981_11
Patent number
US04299618

Reaction notes

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