1,1'-Carbonyldiimidazole → HCID 86683402, compound

HRID 579428Notes

Reaction equation

HRID 579428 reaction equation
[N:1]1([C:6]([N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[O:7])[CH:5]=[CH:4]N=[CH:2]1.[CH3:13][O:14][C:15]1[CH:24]=[CH:23][C:22]2CNCC[C:17]=2[C:16]=1[CH:25]=[O:26]>O1CCCC1>[N:8]1([C:6]([N:1]2[CH2:2][CH2:22][C:17]3[C:16]([CH:25]=[O:26])=[C:15]([O:14][CH3:13])[CH:24]=[CH:23][C:4]=3[CH2:5]2)=[O:7])[CH:12]=[CH:11][N:10]=[CH:9]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 86683401HCID 86683401, compound

Product 1

HCID 86683402HCID 86683402, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of freshly dried di-imidazol-1-yl-methanone (276 mg, 1.7 mmol) in anhydrous tetrahydrofuran (20 mL) the solution of 6-methoxy-1,2,3,4-tetrahydro-isoquinoline-5-carbaldehyde (325 mg, 1.7 mmol) in anhydrous tetrahydrofuran (10 mL) was added and the mixture was stirred at 80° C. oil bath for 14 h. The solution was concentrated and the residue was dissolved in dichloromethane, washed with water (2×10 mL), dried over MgSO4 and concentrated. In this manner the title compound (426 mg, 1.50 mmol, 88.2%) was obtained as a brownish yellow foam.

Workup

  1. concentrationThe solution was concentrated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with water (2×10 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-76683c340a1c48c88d104686bc13defa
Source dataset
uspto-grants-2015_05
Patent number
US09040714B2

Reaction notes

Loading…