Chloride → 1-(2,4 Hexadienoyl) 2-amino benzimidazole

HRID 1252696Notes

Reaction equation

HRID 1252696 reaction equation
[NH2:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.C(N(CC)CC)C.[Cl-].[C:19](O)(=[O:25])[CH:20]=[CH:21][CH:22]=[CH:23][CH3:24]>O1CCCC1.O>[C:19]([N:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[NH2:1])(=[O:25])[CH:20]=[CH:21][CH:22]=[CH:23][CH3:24]

Participants

7

Reactant 4

HCID 312ChlorideHCID 52512,4-Hexadienoic AcidHCID 8471TriethylamineHCID 136242-Aminobenzimidazole

Product 1

HCID 541372271-(2,4 Hexadienoyl) 2-amino benzimidazoleYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-amino benzimidazole (4 g, or 0.030 mole) and triethylamine (4.2 ml, or 0,029 mole) in 70 ml of anhydrous tetrahydrofuran, is chilled to a temperature of between -5° and 0° C. To this solution is slowly added 4 g (0.030 mole) chloride of 2,4 hexadienoic acid in solution in 50 ml of anhydrous tetrahydrofuran. After being agitated, the mixture is left to return to ambiant temperature, after which it is poured into water. The precipitate is drained and washed with water. After recrystallization in toluene, 4.12 g (60% yield) is obtained of a crystallized compound having a melting point of 215° C. and the following structure (90% purity): ##STR4##

Workup

  1. waitthe mixture is left
  2. washwashed with water
  3. customAfter recrystallization in toluene
  4. custom4.12 g (60% yield) is obtained of a crystallized compound

Sources & evidence

ORD record
ord-034b4ac8e6314d2287eecbe132d53f83
Source dataset
uspto-grants-1988_05
Patent number
US04745125

Reaction notes

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