Water → HCID 178477664, compound

HRID 1720288Notes

Reaction equation

HRID 1720288 reaction equation
[CH2:1]([S:3][C:4]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[NH:31][N:30]=[N:29][N:28]=3)=[CH:17][CH:16]=2)[C:7]2=[N:8][CH:9]=[CH:10][C:11]([CH3:12])=[C:6]2[N:5]=1)[CH3:2].ClC1C=CC=C(C(OO)=[O:40])C=1.[OH2:43].C(OCC)(=O)C>ClCCl.CO>[CH2:1]([S:3]([C:4]1[N:13]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[NH:31][N:30]=[N:29][N:28]=3)=[CH:19][CH:20]=2)[C:7]2=[N:8][CH:9]=[CH:10][C:11]([CH3:12])=[C:6]2[N:5]=1)(=[O:40])=[O:43])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 178477329HCID 178477329, compound

Product 1

HCID 178477664HCID 178477664, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

6.4 g (15 mmol) of 2-ethylthio-7-methyl-3[(2'-(1H-tetrazol-5-yl) biphenyl -4-yl) methyl]-3H- imidazo[4.5-b]pyridine was dispersed in 150 ml of dichloromethane. 150 ml of a dichloromethane solution of 3.94 g (23 mmol) of meta-chloro-perbenzoic acid was added dropwise to the solution over 40 minutes, while agitated and cooled with water and ice. The mixture was stirred at room temperature for 20 minutes. The reaction product mixture was washed separately with 10% aqueous solution of sodium bisulfate, a saturated aqueous solution of sodiuim bicarbonate and a saturated saline. The dichloromethane phase was separated and taken, then dried with aqueous magnesium sulfate. The solvent was distilled out at a reduced pressure and the residue was treated chromatographically with silicagel to obtain 5.93 g of the above named compound from the eluate of ethyl acetate and methanol (9:1 v/v).

Workup

  1. stirringThe mixture was stirred at room temperature for 20 minutes
  2. washThe reaction product mixture was washed separately with 10% aqueous solution of sodium bisulfate
  3. customThe dichloromethane phase was separated
  4. dry with materialdried with aqueous magnesium sulfate
  5. distillationThe solvent was distilled out at a reduced pressure
  6. additionthe residue was treated chromatographically with silicagel
  7. customto obtain 5.93 g of the

Sources & evidence

ORD record
ord-61da10113dbb437d96f1306f2535162c
Source dataset
uspto-grants-1996_04
Patent number
US05506238

Reaction notes

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