Ethyl chloroformate → HCID 178473481, compound

HRID 2248276Notes

Reaction equation

HRID 2248276 reaction equation
[CH2:1]([O:3][C:4](Cl)=[O:5])[CH3:2].[NH2:7][CH2:8][CH2:9][CH2:10][C:11]1[NH:15][C:14]2[CH:16]=[CH:17][C:18]([C:20]3[CH:21]([CH3:27])[CH2:22][C:23](=[O:26])[NH:24][N:25]=3)=[CH:19][C:13]=2[N:12]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.O>[CH2:1]([O:3][C:4]([NH:7][CH2:8][CH2:9][CH2:10][C:11]1[NH:15][C:14]2[CH:16]=[CH:17][C:18]([C:20]3[CH:21]([CH3:27])[CH2:22][C:23](=[O:26])[NH:24][N:25]=3)=[CH:19][C:13]=2[N:12]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 178429562HCID 178429562, compound

Product 1

HCID 178473481HCID 178473481, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

0.45 ml (4 7 mmol) of ethylchloroformate are added dropwise over a period of 10 minutes to a solution of 1 00 g (3.5 mmol) of 6-[2-(3-aminopropyl)-1H-benzimidazol-5-yl]-4,5-dihydro -5-methyl-3(2H)-pyridazinone and 1 25 g (9.0 mmol) of potassium carbonate in 10 ml of acetone and 10 ml of water with cooling in an ice bath. After 3 hours' stirring at room temperature, the reaction mixture is filtered and the filtrate is diluted with 20 ml of water and extracted three times with 20 ml portions of dichloromethane. The combined organic phases are dried and concentrated by evaporation under vacuum and the residue is chromatographed on silica gel with dichloromethane/methanol (9:1) as solvent. The polar main fraction (Rf 0 46) yields 0.65 g (52%) of the title compound in the form of a yellowish, amorphous solid after concentration by evaporation under vacuum.

Workup

  1. temperaturewith cooling in an ice bath
  2. filtrationthe reaction mixture is filtered
  3. additionthe filtrate is diluted with 20 ml of water
  4. extractionextracted three times with 20 ml portions of dichloromethane
  5. customThe combined organic phases are dried
  6. concentrationconcentrated by evaporation under vacuum
  7. customthe residue is chromatographed on silica gel with dichloromethane/methanol (9:1) as solvent

Sources & evidence

ORD record
ord-7dc4bf8bffcb4258b53b8f4ff9550c3d
Source dataset
uspto-grants-1991_08
Patent number
US05039675

Reaction notes

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