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

HRID 1154978Notes

Reaction equation

HRID 1154978 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(O)(C)C>O>[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

5

Reactant 3

HCID 3776Isopropanol2×HCID 72122,4-Dichlorobenzyl chlorideHCID 7622Tributylamine2×

Product 1

HCID 165101N,N-Dibutyl-N-[(2,4-dichlorophenyl)methyl]butan-1-aminium chlorideYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

One hundred eighty-five and four-tenths parts of tributylamine and 97.8 parts of 2,4-dichlorobenzyl chloride were mixed with 78.5 parts of isopropanol and placed in a reactor equipped with a stirrer, condenser and thermometer. The mixture was heated for 6 hours with stirring at 80° C. after which the isopropanol and excess tributylamine were removed by distillation at 2 mm. and 80° C. 124.2 parts of crude product were obtained. The crude product was dissolved in 300 parts of water, and the water solution was washed with about 50 parts of hexane. The hexane was separated from the water and the water was removed by distillation, giving a recovery from the wash step of 67% tributyl-2,4-dichlorobenzylammonium chloride. Refractive index at 24° C., 1.529; Ionic Cl (Calc.) 9.31%; Cl (found) 9.34% (Volhard).

Workup

  1. customplaced in a reactor
  2. customequipped with a stirrer, condenser
  3. temperatureThe mixture was heated for 6 hours
  4. customwere removed by distillation at 2 mm
  5. custom80° C
  6. custom124.2 parts of crude product were obtained
  7. washthe water solution was washed with about 50 parts of hexane
  8. customThe hexane was separated from the water
  9. customthe water was removed by distillation

Sources & evidence

ORD record
ord-c555180d1f9943279e2cdfcac487cbc4
Source dataset
uspto-grants-1981_11
Patent number
US04299618

Reaction notes

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