Potassium Carbonate → HCID 15166240, compound

HRID 727890Notes

Reaction equation

HRID 727890 reaction equation
[SH:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.Cl[CH2:12][C:13]1[C:18]([CH3:19])=[C:17]([O:20][CH2:21][CH2:22][N:23]2[C:27](=[O:28])[CH2:26][CH2:25][C:24]2=[O:29])[CH:16]=[CH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH3:19][C:18]1[C:13]([CH2:12][S:1][C:2]2[NH:6][C:5]3[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=3[N:3]=2)=[N:14][CH:15]=[CH:16][C:17]=1[O:20][CH2:21][CH2:22][N:23]1[C:27](=[O:28])[CH2:26][CH2:25][C:24]1=[O:29]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15166219HCID 15166219, compoundHCID 178527775HCID 178527775, compound

Product 1

HCID 15166240HCID 15166240, compoundYield 112.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture comprising 0.03 g (0.18 mmol) of 2-mercapto-1H-benzimidazole, 0.06 g (0.21 mmol) of 2-chloromethyl-3-methyl-4-(2-succinimidoethoxy)pyridine, 0.03 g (0.21 mmol) of potassium carbonate and 10 ml of methyl ethyl ketone was heated under reflux in a nitrogen atmosphere for 3 hours, cooled and filtered. The filtrate was concentrated and dried in a vacuum, followed by the addition of water. The obtained mixture was extracted with 50 ml of chloroform thrice. The extract was dried over magnesium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography to obtain 0.08 g of 2-[{3-methyl-4-(2-succinimidoethoxy)pyridine-2-yl}methylthio]-1H-benzimidazole as a white crystal.

Workup

  1. temperatureunder reflux in a nitrogen atmosphere for 3 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customdried in a vacuum
  6. additionfollowed by the addition of water
  7. extractionThe obtained mixture was extracted with 50 ml of chloroform thrice
  8. dry with materialThe extract was dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated
  11. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-7c6acba59ee64bf6b674cb1ef6f62218
Source dataset
uspto-grants-1991_09
Patent number
US05045552

Reaction notes

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