Sodium Iodide → HCID 22508768, compound

HRID 984793Notes

Reaction equation

HRID 984793 reaction equation
[C:1]([NH:4][C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][C:6]=1[NH2:16])(=O)[CH3:2].C([O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[C:23]([Cl:29])[CH:22]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>O.C(OCC)(=O)C>[Cl:29][C:23]1[CH:22]=[C:21]([OH:20])[CH:28]=[CH:27][C:24]=1[CH2:25][N:16]1[C:6]2[CH:7]=[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:14]=[CH:15][C:5]=2[N:4]=[C:1]1[CH3:2]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 12051751HCID 12051751, compoundHCID 223879114-Acetoxy-2-chlorobenzylbromide

Product 1

HCID 22508768HCID 22508768, compoundYield 15.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 6.34 g of ethyl 4-(acetylamino)-3-amino-benzoate, 14.0 g of 4-acetoxy-2-chlorobenzyl bromide, 5.12 g of potassium carbonate, 1.28 g of sodium iodide, 35 ml of ethyl acetate, and 13 ml of water was stirred at 70° C. for 15 hours. After the reaction was completed, the solution was separated. After washed with water, the organic layer was concentrated under reduced pressure. To the oily residue, 30 ml of ethanol and 3.2 g of 35% hydrochloric acid was added and the solution was stirred at 70° C. for 3 hours. The reaction solution was extracted with ethyl acetate and water. The organic layer was concentrated, and, for crystallization, ethanol was added to the residue obtained. The crystals obtained through filtration were dried to give 1.53 g of 1-(2-chloro-4-hydroxybenzyl)-6-(ethoxycarbonyl)-2-methylbenzimidazole. The filtrate was concentrated, and, for crystallization, ethanol was added to the residue obtained. The crystals obtained through filtration were dried to give 4.72 g of 1-(2-chloro-4-hydroxybenzyl)-6-(ethoxycarbonyl)-2-methylbenzimidazole.

Workup

  1. customthe solution was separated
  2. washAfter washed with water
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. additionTo the oily residue, 30 ml of ethanol and 3.2 g of 35% hydrochloric acid was added
  5. stirringthe solution was stirred at 70° C. for 3 hours
  6. extractionThe reaction solution was extracted with ethyl acetate and water
  7. concentrationThe organic layer was concentrated
  8. customfor crystallization, ethanol
  9. additionwas added to the residue
  10. customobtained
  11. customThe crystals obtained through filtration
  12. customwere dried

Sources & evidence

ORD record
ord-71f5e93a730d44acb13fdca7438bdfa0
Source dataset
uspto-grants-2005_03
Patent number
US06869950B1

Reaction notes

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