Triethylamine → HCID 19600553, compound

HRID 727928Notes

Reaction equation

HRID 727928 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][S:14][C:15]2[N:19]([CH3:20])[C:18]3[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=3[N:16]=2)[C:8]=1[CH3:25].ClC1C=CC=C(C(OO)=[O:34])C=1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>ClCCl>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][S:14]([C:15]2[N:19]([CH3:20])[C:18]3[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=3[N:16]=2)=[O:34])[C:8]=1[CH3:25]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 15166338HCID 15166338, compound

Product 1

HCID 19600553HCID 19600553, compoundYield 45.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.25 g of 2-{4-(3-methoxypropoxy)-3-methylpyridine-2-yl}methylthio-1-methylbenzimidazole was dissolved in 20 ml of dichloromethane to obtain a solution. 0.18 g of 80% m-chloroperbenzoic acid was added to the solution at -50° C. The obtained mixture was stirred for one hour, followed by the addition of 0.14 g of triethylamine and 20 ml of a saturated aqueous solution of sodium hydrogencarbonate. The obtained mixture was stirred at a room temperature for one hour. The dichloromethane layer was separated, washed with a saturated aqueous solution of sodium hydrogencarbonate twice, dried over magnesium sulfate and filtered. The filtrate was concentrated to obtain a residue. This residue was purified by silica gel column chromatography to obtain 0.12 g of the title compound as a pale yellow crystal.

Workup

  1. customto obtain a solution
  2. stirringThe obtained mixture was stirred at a room temperature for one hour
  3. customThe dichloromethane layer was separated
  4. washwashed with a saturated aqueous solution of sodium hydrogencarbonate twice
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customto obtain a residue
  9. customThis residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f920073494134dc39619bbdb89df8435
Source dataset
uspto-grants-1991_09
Patent number
US05045552

Reaction notes

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