Ammonia → HCID 13881505, compound

HRID 1164435Notes

Reaction equation

HRID 1164435 reaction equation
[N:1]#[C:2]Br.[CH3:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[NH:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]1[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:24].O.N>C(O)CCC>[CH3:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[N:12]1[CH2:13][CH2:14][CH2:15][N:16]([C:17]2[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:24])[C:2]1=[NH:1]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 10476Cyanogen BromideHCID 10959275HCID 10959275, compound

Product 1

HCID 13881505HCID 13881505, compoundYield 36.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

A solution of 0.75 g (7.1 mmoles) of cyanogen bromide in 10 ml of n-butanol is added dropwise, within about 0.5 hours, to a stirred solution of 2.0 g (7.1 mmole) of 1,3-bis(2',6'-dimethylphenyl-amino)-propane in 20 ml of n-butanol at 110° to 115° C. After the addition the mixture is stirred for further 2 hours at the same temperature. Thereafter the mixture is cooled, shaken five times with 10 ml of water each, the aqueous solutions are combined, and the pH of the mixture is adjusted to 8.0 to 8.5 with concentrated aqueous ammonia. The separated unreacted starting substance (0.4 g, m.p.: 68°-71° C.) is filtered off, the aqueous filtrate is rendered alkaline with 2 n aqueous sodium hydroxide solution, and the aqueous-alkaline phase is extracted thrice with 30 ml of chloroform each. The organic phases are combined, washed with water, dried over potassium carbonate, and the solvent is distilled off. 0.8 g (36.7%) of 1,3-bis(2',6'-dimethylphenyl)-2-imino-hexahydro-pyrimidine are obtained; m.p.: 181°-183° C. (after recrystallization from aqueous isopropenol).

Workup

  1. additionAfter the addition the mixture
  2. temperatureThereafter the mixture is cooled
  3. filtrationis filtered off
  4. extractionthe aqueous-alkaline phase is extracted thrice with 30 ml of chloroform each
  5. washwashed with water
  6. dry with materialdried over potassium carbonate
  7. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-000cc4955369450883519c863bc21324
Source dataset
uspto-grants-1983_01
Patent number
US04369325

Reaction notes

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