Potassium Carbonate → HCID 19347995, compound

HRID 1637205Notes

Reaction equation

HRID 1637205 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:9]=[CH:10][C:11]2[C:15]([S:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:17])=[C:14]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[S:13][C:12]=2[CH:29]=1.Cl.Cl[CH2:32][C:33]1[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=1>CN(C)C=O>[CH3:1][O:4][C:20]1[CH:19]=[C:18]([S:16]([C:15]2[C:11]3[CH:10]=[CH:9][C:8]([O:7][CH2:32][C:33]4[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=4)=[CH:29][C:12]=3[S:13][C:14]=2[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:17])[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 745704-(Chloromethyl)pyridinium chlorideHCID 19347976HCID 19347976, compound

Product 1

HCID 19347995HCID 19347995, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (240 mg, 1.73 mmol) was added to a solution of ethyl 6-hydroxy-3-(phenylsulfinyl)benzo[b]thiophene-2-carboxylate (Preparation 19, 200 mg, 0.58 mmol) in anhydrous dimethylformamide (3 ml) at ambient temperature under a nitrogen atmosphere. After 15 minutes 4-(chloromethyl)pyridine hydrochloride (104 mg, 0.64 mmol) was added, and stirring continued for 24 hours. The mixture was partitioned between ethyl acetate and water, and the organic layer was separated and washed twice with water, dried (magnesium sulfate), and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel using ethyl acetate as eluant, and crystallised from diisopropyl ether to give the title compound as a colourless solid (198 mg).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customthe organic layer was separated
  3. washwashed twice with water
  4. dry with materialdried (magnesium sulfate)
  5. customevaporated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel
  7. customcrystallised from diisopropyl ether

Sources & evidence

ORD record
ord-aff5646334d040ceb861510b280ca052
Source dataset
uspto-grants-2000_03
Patent number
US06040309

Reaction notes

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