Potassium Carbonate → HCID 23432914, compound

HRID 2121353Notes

Reaction equation

HRID 2121353 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:9][C:4]=2[NH:3][CH:2]=1.Cl[CH2:16][CH2:17][N:18]([CH2:21][CH3:22])[CH2:19][CH3:20].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:17]([N:18]([CH2:21][CH2:22][N:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:9][C:4]=2[N:3]=[CH:2]1)[CH2:19][CH3:20])[CH3:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13364Diethylaminoethyl chlorideHCID 13505555Ethyl 1H-benzimidazole-6-carboxylate

Product 1

HCID 23432914HCID 23432914, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.4 g (28.4 mmol) of ethyl benzimidazole-5-carboxylate, 9.8 g (56.8 mmol) of N-(2-chloro-1-ethyl)-N,N-diethylamine and 7.9 g (56.8 mmol) of potassium carbonate were heated in 100 ml of dimethylformamide at 100° C. for 4 hours. The mixture was then filtered, the filtrate was concentrated in vacuo, and the resulting residue was purified by chromatography (mobile phase: ethyl acetate/acetone=1/1). 2.6 g of an isomer mixture containing ethyl 3-(2-(N,N-diethylamino)-1-ethyl)benzimidazole-5-carboxylate in addition to the product were obtained.

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customthe resulting residue was purified by chromatography (mobile phase: ethyl acetate/acetone=1/1)
  4. addition2.6 g of an isomer mixture containing ethyl 3-(2-(N,N-diethylamino)-1-ethyl)benzimidazole-5-carboxylate
  5. additionin addition to the product
  6. customwere obtained

Sources & evidence

ORD record
ord-9bc46e9934db45cdab80184668b6673c
Source dataset
uspto-grants-2004_02
Patent number
US06696437B1

Reaction notes

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