Sodium Hydroxide → HCID 11671669, compound

HRID 1820848Notes

Reaction equation

HRID 1820848 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[N:13]=[C:14]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[S:15][C:16]=3[Br:17])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:24][CH:25]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:26]([O:28]C)=[O:27].[OH-].[Na+]>C1COCC1.CO.O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[N:13]=[C:14]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[S:15][C:16]=3[Br:17])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:24][CH:25]([CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:26]([OH:28])=[O:27]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 68981964HCID 68981964, compound

Product 1

HCID 11671669HCID 11671669, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 2-{[1-bromo-6-(5-bromo-2-phenyl-1,3-thiazol-4-yl)-2-naphthyl]oxy}-3-phenylpropanoate (134 mg, 0.215 mmol), prepared in the previous step, and 1 N NaOH (323 μL, 0.323 mmol) in 10 mL of THF plus 10 mL of methanol plus 5 mL of water was refluxed under nitrogen 2 h. The reaction was filtered, acidified with 1 N HCl and then concentrated under reduced pressure to remove the THF and methanol. The solid present was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound (68 mg, 52%) as a yellow solid, mp 221-223° C. Elemental Analysis for C28H19Br2NO3S Calc'd: C, 55.19; H, 3.14; N, 2.30. Found: C, 56.17; H, 3.45; N, 2.05.

Workup

  1. temperaturewas refluxed under nitrogen 2 h
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated under reduced pressure
  4. customto remove the THF and methanol
  5. filtrationThe solid present was collected by filtration
  6. washrinsed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-b2a1adfe1b444e14bf2175785b708809
Source dataset
uspto-grants-2009_10
Patent number
US07605172B2

Reaction notes

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