Dichloromethane → HCID 13228938, compound

HRID 1380551Notes

Reaction equation

HRID 1380551 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:5]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18]C)=[C:14]([CH3:20])[CH:13]=2)[C:6]=1[CH2:7][C:8]([OH:10])=[O:9].ClCCl.[Cl-].[Al+3].[Cl-].[Cl-]>C(O)C>[Cl:1][C:2]1[N:3]=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:5]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([CH3:20])[CH:13]=2)[C:6]=1[CH2:7][C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6451240Aluminum(III) ChlorideHCID 12822158HCID 12822158, compound

Product 1

HCID 13228938HCID 13228938, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Chloro-1-(4-methoxy-3-methylbenzyl)-2-phenylimidazole-5-acetic acid (15 g) was added to 270 ml of a dichloromethane solution containing 16.2 g of aluminum chloride and 10 g of 1,3-ethanedithiol and the mixture was stirred at room temperature, whereupon the starting material dissolved once and then a precipitate separated out. The mixture was allowed to stand at room temperature for 6 hours. The supernatant was then discarded, and 50 ml of acetone and 20 ml of water were added to the precipitate. To the resulting solution was added 20 ml of lN-hydrochloric acid to give a precipitate, which was dissolved in 150 ml of 75% ethanol. The solution was passed through a column of 50 ml of Amberlite IRC-50 (trademark) (H-form) and the column was washed with 75% ethanol. The effluent and washings were combined and diluted with water to the ethanol concentration of 50%. The above procedure gave 12 g of 4-chloro-1-(4-hydroxy-3-methylbenzyl)-2-phenylimidazole-5-acetic acid as colorless scales, m.p. 190°-192 ° C. (decompn.).

Workup

  1. dissolutiondissolved once
  2. customa precipitate separated out
  3. addition50 ml of acetone and 20 ml of water were added to the precipitate
  4. additionTo the resulting solution was added 20 ml of lN-hydrochloric acid
  5. customto give a precipitate, which
  6. washthe column was washed with 75% ethanol
  7. additiondiluted with water to the ethanol concentration of 50%

Sources & evidence

ORD record
ord-9f9c7a6b30d74187a99120fc4e92b5fc
Source dataset
uspto-grants-1986_04
Patent number
US04582847

Reaction notes

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