Triethylamine → HCID 19600534, compound

HRID 727930Notes

Reaction equation

HRID 727930 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[S:15][CH2:16][C:17]1[C:22]([CH3:23])=[C:21]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:20]=[CH:19][N:18]=1)=[O:5])[CH3:2].ClC1C=CC=C(C(OO)=[O:38])C=1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>ClCCl>[CH2:1]([O:3][C:4]([N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[S:15]([CH2:16][C:17]1[C:22]([CH3:23])=[C:21]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:20]=[CH:19][N:18]=1)=[O:38])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 15166340HCID 15166340, compound

Product 1

HCID 19600534HCID 19600534, compoundYield 33.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.6 g of 1-ethoxycarbonyl-2-{4-(3-methoxypropoxy)-3-methylpyridine-2-yl}methylthiobenzimidazole was dissolved in 20 ml of dichloromethane to obtain a solution. 0.4 g of m-chloroperbenzoic acid was added to the solution at -45° C. After one hour, 0.3 g of triethylamine and 20 ml of a saturated aqueous solution of sodium hydrogencarbonate were added to the resulting mixture. The obtained mixture was stirred at a room temperature for 30 minutes. 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 0.21 g of the title compound as a yellow oil.

Workup

  1. customto obtain a solution
  2. customThe dichloromethane layer was separated
  3. washwashed with a saturated aqueous solution of sodium hydrogencarbonate twice
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customto obtain a residue
  8. customThis residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6eda792404c146a5aa335cf75c34aa98
Source dataset
uspto-grants-1991_09
Patent number
US05045552

Reaction notes

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