Methanol → (3-Chloropropyl)tetradecyldimethylammonium bromide

HRID 1075403

Reaction equation

HRID 1075403 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH3:3].[Br:18][CH2:19][CH2:20][CH2:21][Cl:22].CO>COC(C)(C)C>[Br-:18].[Cl:22][CH2:21][CH2:20][CH2:19][N+:2]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 80061-Bromo-3-chloropropaneHCID 8211N,N-Dimethyltetradecylamine

Product 1

HCID 85711139(3-Chloropropyl)tetradecyldimethylammonium bromide

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
65 °C

Procedure

A one-liter, 3-necked, round-bottomed flask equipped with air condensers and a magnetic stirring plate was charged with N,N-dimethyltetradecylamine (311.59 grams, 1.29 moles), 1-bromo-3-chloropropane (203.09 grams, 1.29 moles) and methanol (250 mL). Reaction was maintained at 65° C. for 24 hours. Methanol was removed by rotary evaporation under reduced pressure to yield a sludge. To the sludge was added methyl-tert-butylether (500 mL) causing a white solid to slowly form The mixture was stirred for one-half hour and white, paste-like particulate was collected by vacuum filtration. The solid was placed in a vacuum oven at 35° C. for 24 hours. Yield 420 grams (1.05 molest 82%).

Workup

  1. customA one-liter, 3-necked, round-bottomed flask equipped with air condensers
  2. customReaction
  3. customMethanol was removed by rotary evaporation under reduced pressure
  4. customto yield a sludge
  5. customto slowly form The mixture
  6. filtrationwas collected by vacuum filtration

Sources & evidence

ORD record
ord-41cfeb4525a347ab85345387371c20d4
Source dataset
uspto-grants-1999_05
Patent number
US05900475

Linked notes

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