Butyl bromide → N,N,N',N',N'',N''-hexa-n-butylguanidinium bromide

HRID 625161

Reaction equation

HRID 625161 reaction equation
[CH2:1]([N:5]([CH2:21][CH2:22][CH2:23][CH3:24])[C:6](=[N:16][CH2:17][CH2:18][CH2:19][CH3:20])[N:7]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:8][CH2:9][CH2:10][CH3:11])[CH2:2][CH2:3][CH3:4].[Br:25][CH2:26][CH2:27][CH2:28][CH3:29]>C(#N)C(C)C>[Br-:25].[CH2:21]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]([N:16]([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:17][CH2:18][CH2:19][CH3:20])=[N+:7]([CH2:8][CH2:9][CH2:10][CH3:11])[CH2:12][CH2:13][CH2:14][CH3:15])[CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 8002Butyl bromideHCID 189218Guanidine, pentabutyl-

Product 1

HCID 11123625N,N,N',N',N'',N''-hexa-n-butylguanidinium bromide

Reagents, catalysts & solvents 1

HCID 6559IsobutyronitrileSolvent

Procedure

A mixture of 1.7 grams (5 mmol) of penta-n-butylguanidine (made as described earlier), 0.686 grams (5 mmol) of 1-bromobutane and 10 ml of isobutyronitrile was heated under reflux for 20 hours. Upon vacuum stripping, a pale yellow oil was obtained which crystallized to a pale brown solid upon standing. Upon recrystallization from a mixture of hexane and ethyl acetate, the desired N,N,N′,N′,N″,N″-hexa-n-butylguanidinium bromide was obtained as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 hours
  3. customUpon vacuum stripping, a pale yellow oil was obtained which
  4. customcrystallized to a pale brown solid
  5. customUpon recrystallization
  6. additionfrom a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-0b044c4e889842178705d0183d506feb
Source dataset
uspto-grants-2016_04
Patent number
US09303201B2

Linked notes

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