2-Methoxyethylamine → HCID 19373124, compound

HRID 129006Notes

Reaction equation

HRID 129006 reaction equation
C[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]([OH:24])=O)=[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][O:26][CH2:27][CH2:28][NH2:29]>O1CCCC1>[CH3:25][O:26][CH2:27][CH2:28][NH:29][C:22](=[O:24])[CH2:21][C:11]1[N:4]2[C:3]([NH:2][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=32)=[N:13][C:12]=1[C:14]1[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 19373106HCID 19373106, compound

Product 1

HCID 19373124HCID 19373124, compoundYield 7.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 3.5 g (0.11 mol) of 9-methyl-2-(4-methylphenyl)-9H-imidazo[1,2-a]benzimidazole-3-acetic acid is prepared in 70 ml of dry tetrahydrofuran, 2.67 g (0.165 mol) of N,N'-carbonyldiimidazole are added in small portions, over 10 min, and the mixture is stirred at room temperature for 1 h. It is cooled in an ice-cold water bath, and 1.65 g (0.165 mol) of 2-methoxyethylamine in solution in 4 ml of dry tetrahydrofuran are added. Stirring is continued for 1 h at cold temperature, and then at room temperature for 4 h. The solvent is evaporated under reduced pressure. The residue is crystallized from water. The solid is collected by filtration, washed, dried and recrystallized from ethanol. 2.9 g of compound are finally obtained. Melting point: 189°-190° C.

Workup

  1. temperatureIt is cooled in an ice-cold water bath
  2. stirringStirring
  3. waitis continued for 1 h at cold temperature
  4. waitat room temperature for 4 h
  5. customThe solvent is evaporated under reduced pressure
  6. customThe residue is crystallized from water
  7. filtrationThe solid is collected by filtration
  8. washwashed
  9. customdried
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-674b3417d6e7440bb64509562de5dcba
Source dataset
uspto-grants-1995_11
Patent number
US05466706

Reaction notes

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