Triethylamine → HCID 178522952, compound

HRID 1071998Notes

Reaction equation

HRID 1071998 reaction equation
Cl.Cl.[NH:3]1[C:11]2[CH2:10][CH2:9][NH:8][CH2:7][C:6]=2[N:5]=[CH:4]1.C(N(CC)CC)C.[Cl:19][C:20]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:21]=1[CH2:22][N:23]=[C:24]=[O:25]>C(O)C>[Cl:19][C:20]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:21]=1[CH2:22][NH:23][C:24]([N:8]1[CH2:9][CH2:10][C:11]2[NH:3][CH:4]=[N:5][C:6]=2[CH2:7]1)=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 46127082,4-Dichlorobenzyl isocyanateHCID 164180044,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine--hydrogen chloride (1/2)

Product 1

HCID 178522952HCID 178522952, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 4,5,6,7-tetrahydroimidazo[4,5-c]pyridine dihydrochloride (0.50 g, 2.55 mmol), ethanol (10 mL) and triethylamine (1.10 mL, 7.89 mmol), 2,4-dichlorobenzyl isocyanate (0.52 g, 2.57 mmol) was added. The resulting mixture was stirred at room temperature for 16 h and then concentrated under reduced pressure. The residue was distributed between water (20 mL) and ethyl acetate (75 mL). The organic phase was washed with water (10 mL) and brine (10 mL), dried (MgSO4) and concentrated under reduced pressure. The residue was triturated in diethylether (50 mL) and the crude product was filtered off. Recrystallization from acetone (25 mL) gave 0.30 g (37%) of the title urea as a colourless solid.

Workup

  1. additionwas added
  2. concentrationconcentrated under reduced pressure
  3. washThe organic phase was washed with water (10 mL) and brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated in diethylether (50 mL)
  7. filtrationthe crude product was filtered off
  8. customRecrystallization from acetone (25 mL)

Sources & evidence

ORD record
ord-05512a3be2834b409d2d52b1282b104e
Source dataset
uspto-grants-2005_06
Patent number
US06908926B1

Reaction notes

Loading…