Sodium Hydroxide → HCID 11728935, compound

HRID 1637206Notes

Reaction equation

HRID 1637206 reaction equation
[OH-].[Na+].[C:3]1([S:9][C:10]2[C:11]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)=[CH:20][C:12]=3[S:13][C:14]=2[C:15]([O:17]CC)=[O:16])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O1CCOCC1>[C:3]1([S:9][C:10]2[C:11]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)=[CH:20][C:12]=3[S:13][C:14]=2[C:15]([OH:17])=[O:16])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9931973HCID 9931973, compound

Product 1

HCID 11728935HCID 11728935, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydroxide (0.5 ml of 2M in water) was added to a solution of ethyl 3-(phenylsulfanyl)-6-(3-pyridylmethoxy)benzo[b]thiophene-2-carboxylate (Example 1, 190 mg, 0.45 mmol) in 1,4-dioxane, and the mixture heated to 60° C. for 4 hours. The solvents were removed under reduced pressure, and the residue was dissolved in water (15 ml) and washed with ethyl acetate (25 ml). The aqueous layer was separated and acidified by dropwise addition of acetic acid until a white solid precipitated. The solid was isolated by filtration and dried under vacuo to give the title compound as a colourless solid (140 mg).

Workup

  1. customThe solvents were removed under reduced pressure
  2. dissolutionthe residue was dissolved in water (15 ml)
  3. washwashed with ethyl acetate (25 ml)
  4. customThe aqueous layer was separated
  5. additionacidified by dropwise addition of acetic acid until a white solid
  6. customprecipitated
  7. customThe solid was isolated by filtration
  8. customdried under vacuo

Sources & evidence

ORD record
ord-3e8b41e8ee1d4fa68f1ba0a8a7e1524d
Source dataset
uspto-grants-2000_03
Patent number
US06040309

Reaction notes

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