Sodium Iodide → 1-(2-Chloro-4-hydroxybenzyl)-6-(ethoxycarbonyl)-2-methylbenzimidazole

HRID 2229466Notes

Reaction equation

HRID 2229466 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+]>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

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 12051751Ethyl 4-(acetylamino)-3-aminobenzoateHCID 223879114-Acetoxy-2-chlorobenzylbromide

Product 1

HCID 225087681-(2-Chloro-4-hydroxybenzyl)-6-(ethoxycarbonyl)-2-methylbenzimidazoleYield 15.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

Ethyl 4-(acetylamino)-3-aminobenzoate (6.34 g), 4-acetoxy-2-chlorobenzyl bromide (14.0 g), potassium carbonate (5.12 g), and sodium iodide (1.28 g) were added to ethyl acetate (35 ml) and uo (13 ml) and the whole was stirred for 15 hours at 70° C. The organic layer was separated, washed with water, and concentrated under reduced pressure. Ethanol (30 ml) and 35% hydrochloric acid (3.2 g) were added to the oily residue and the mixture was stirred for 3 hours at 70° C. After extraction of the reaction solution with ethyl acetate and water, the organic layer was separated and concentrated. The residue was crystallized by addition of ethanol. Crystals obtained by filtration was dried to obtain 1-(2-chloro-4-hydroxybenzyl)-6-(ethoxycarbonyl)-2-methylbenzimidazole (1.53 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. concentrationconcentrated under reduced pressure
  4. additionEthanol (30 ml) and 35% hydrochloric acid (3.2 g) were added to the oily residue
  5. stirringthe mixture was stirred for 3 hours at 70° C
  6. extractionAfter extraction of the reaction solution with ethyl acetate and water
  7. customthe organic layer was separated
  8. concentrationconcentrated
  9. customThe residue was crystallized by addition of ethanol
  10. customCrystals obtained by filtration
  11. customwas dried

Sources & evidence

ORD record
ord-f4566975881f42d6bfde56125a880d34
Source dataset
uspto-grants-2002_07
Patent number
US06420409B1

Reaction notes

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