Triethylamine → HCID 15166247, compound

HRID 609834Notes

Reaction equation

HRID 609834 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1[C:14]([CH2:30][S:31][C:32]2[NH:36][C:35]3[CH:37]=[CH:38][CH:39]=[CH:40][C:34]=3[N:33]=2)=[N:15][CH:16]=[CH:17][C:18]=1[O:19][CH2:20][CH2:21][O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>ClCCl>[CH3:12][C:13]1[C:14]([CH2:30][S:31]([C:32]2[NH:33][C:34]3[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=3[N:36]=2)=[O:9])=[N:15][CH:16]=[CH:17][C:18]=1[O:19][CH2:20][CH2:21][O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 15166246HCID 15166246, compound

Product 1

HCID 15166247HCID 15166247, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

0.16 g of m-chloroperbenzoic acid was added to a solution of 0.38 g of 2-[{3-methyl-4-(2-pyridylmethoxyethoxy)pyridine-2-yl}methylthio]-1H-benzimidazole in 20 ml of dichloromethane at -60° C. in a nitrogen atmosphere to obtain a mixture. This mixture was stirred for 0.5 hour. After the completion of the reaction, 0.16 g of triethylamine was added to the reaction mixture. The obtained mixture was heated to -10° C., followed by the addition of 30 ml of a saturated aqueous solution of sodium hydrogencarbonate. The obtained mixture was stirred at a room temperature for 0.5 hour and extracted with 50 ml of dichloromethane thrice. The extract was dried over magnesium sulfate and filtered. The filtrate was concentrated and dried in a vacuum to obtain a crude product. This crude product was crystallized from dichloromethane/diethyl ether to obtain 0.31 g of 2-[{3-methyl-4-(2-pyridylmethoxyethoxy)pyridine-2-yl}methylsulfinyl]-1H-benzimidazole as a white crystal.

Workup

  1. customto obtain a mixture
  2. additionwas added to the reaction mixture
  3. stirringThe obtained mixture was stirred at a room temperature for 0.5 hour
  4. extractionextracted with 50 ml of dichloromethane thrice
  5. dry with materialThe extract was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customdried in a vacuum
  9. customto obtain a crude product
  10. customThis crude product was crystallized from dichloromethane/diethyl ether

Sources & evidence

ORD record
ord-e9a322fc5d8447d3a98d6385ff43527d
Source dataset
uspto-grants-1999_12
Patent number
US05998445

Reaction notes

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