Methylamine → HCID 15227895, compound

HRID 128996Notes

Reaction equation

HRID 128996 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]2[C:11]([CH2:21][C:22](O)=[O:23])=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)[N:13]=[C:3]12.[CH3:25][NH2:26]>O1CCCC1>[CH3:25][NH:26][C:22](=[O:23])[CH2:21][C:11]1[N:4]2[C:3]([N:2]([CH3:1])[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=32)=[N:13][C:12]=1[C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 19373106HCID 19373106, compound

Product 1

HCID 15227895HCID 15227895, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 1.9 g (0.006 mol) of 9-methyl-2-(4-methylphenyl)-9H-imidazo[1,2-a]benzimidazole-3-acetic acid is prepared in 50 ml of dry tetrahydrofuran, 1.45 g (0.009 mol) of N,N'-carbonyldiimidazole are added, in small portions, under an inert atmosphere and the mixture is stirred at room temperature for 2 h. The mixture is cooled in an ice-cold water bath, and treated with an excess of dry methylamine. Stirring is maintained for 16 h at room temperature. The solvent is evaporated under reduced pressure, and the residue is taken up in water, separated by filtration, washed with water, dried under vacuum and purified by recrystallization from methanol. 1 g of compound is obtained. Melting point: 251°-252° C.

Workup

  1. temperatureThe mixture is cooled in an ice-cold water bath
  2. stirringStirring
  3. temperatureis maintained for 16 h at room temperature
  4. customThe solvent is evaporated under reduced pressure
  5. customseparated by filtration
  6. washwashed with water
  7. customdried under vacuum
  8. custompurified by recrystallization from methanol

Sources & evidence

ORD record
ord-5739e23fffd5440fb8547c1e7057445b
Source dataset
uspto-grants-1995_11
Patent number
US05466706

Reaction notes

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