Water → HCID 21397137, compound

HRID 1414729Notes

Reaction equation

HRID 1414729 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][NH:11][C:12]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:13]=2[NH2:14])[CH2:4][CH2:3]1.O.[N:21]#[C:22]Br.[OH-].[Na+]>C(O)C>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:8][CH2:9][CH2:10][N:11]2[C:12]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:13]=3[N:14]=[C:22]2[NH2:21])[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 14798Sodium HydroxideHCID 14319499HCID 14319499, compound

Product 1

HCID 21397137HCID 21397137, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-[3-(4-methyl-1-piperazinyl)propylamino]-5-chloroaniline (70 g., 0.248 mole) in 350 ml. of water and 150 ml. ethanol was added, with stirring, 59.0 g. (0.557 mole) of cyanogen bromide in portions over 1 hour. The temperature was maintained at 40°-50° C. After the addition was completed the mixture was allowed to cool to room temperature and stirred overnight. After pouring into 1500 ml. ice water and making strongly alkaline with 20% NaOH, the precipitated solid was collected on a Buchner funnel, washed with water and dried in the vacuum oven to obtain 45.0 g. (59% yield) of crude 1-[3-(4-methyl-1-piperazinyl)propyl]-2-amino-5-chlorobenzimidazole, m.p. 223°-227° C. A portion was recrystallized from acetone as colorless needles, m.p. 228°-229.5° C.

Workup

  1. temperatureThe temperature was maintained at 40°-50° C
  2. additionAfter the addition
  3. stirringstirred overnight
  4. additionAfter pouring into 1500 ml
  5. customthe precipitated solid was collected on a Buchner funnel
  6. washwashed with water
  7. customdried in the vacuum oven
  8. customto obtain 45.0 g

Sources & evidence

ORD record
ord-bed5fe18644f403dacbd90e40dc64c49
Source dataset
uspto-grants-1977_01
Patent number
US04002623

Reaction notes

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