Acetonitrile → HCID 10949546, compound

HRID 1655811Notes

Reaction equation

HRID 1655811 reaction equation
[CH2:1]([N:15]([CH3:17])[CH3:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C(#N)C.[Br:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>>[Br-:21].[CH2:1]([N+:15]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])([CH3:17])[CH3:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 81011-BromohexaneHCID 8211N,N-Dimethyltetradecylamine

Product 1

HCID 10949546HCID 10949546, compound

Conditions

Temperature
85 °C

Procedure

The following are added successively at room temperature with stirring to a flask of contents 1 dm3 which is equipped with a stirrer, a reflux condenser and a contact thermometer and is surrounded at its bottom by an electrically heatable jacket which is controlled by the contact thermometer: 145.3 g (0.6 mol) of N-tetradecyl-N,N-dimethylamine, 249.3 g (6.07 mol) of acetonitrile and 104.0 g (0.63 mol) of 1-bromohexane. While stirring is continued, the mixture is heated to a temperature of 85° C. and kept at this temperature for 4 hours, then it is cooled to room temperature, a sample is taken and the residual amine content in this is determined. On the basis of this determination, the amine conversion is 99%. The contents of the flask are then added to a rotary evaporator and the liquid constituents, essentially acetonitrile, are distilled off in a water bath at a temperature rising from 50° to 80° C. and a pressure falling from 9.6 to 1.8 kPa at 320 revolutions per minute during the course of 4 hours. The N-tetradecyl-N-hexyl-N,N-dimethylammonium bromide (1) thus obtained is then dried at room temperature under a pressure of 40 Pa generated by an oil vacuum pump and used for the viscosity determinations described below. The product is analysed, the following values being determined:

Workup

  1. additionThe following are added successively at room temperature
  2. customis equipped with a stirrer, a reflux condenser
  3. stirringWhile stirring
  4. temperatureit is cooled to room temperature
  5. additionThe contents of the flask are then added to a rotary evaporator
  6. distillationthe liquid constituents, essentially acetonitrile, are distilled off in a water bath at a temperature
  7. customrising from 50° to 80° C.
  8. customfalling from 9.6 to 1.8 kPa at 320 revolutions per minute during the course of 4 hours

Sources & evidence

ORD record
ord-0d095c2f2ce04708ae92e88dcd766d22
Source dataset
uspto-grants-1993_10
Patent number
US05252257

Reaction notes

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