Sodium Hydroxide → HCID 11640728, compound

HRID 1820843Notes

Reaction equation

HRID 1820843 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[N:13]=[C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[S:15][CH:16]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:23][CH2:24][C:25]([O:27]C)=[O:26].[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:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[S:15][CH:16]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:23][CH2:24][C:25]([OH:27])=[O:26]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 86603572HCID 86603572, compound

Product 1

HCID 11640728HCID 11640728, compoundYield 92.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl {[1-bromo-6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthyl]oxy}acetate (217 mg, 0.477 mmol), prepared in the previous step, and 1 N NaOH (716 μL, 0.716 mmol) in 20 mL of THF plus 20 mL of methanol plus 10 mL of water was refluxed under nitrogen for 2.25 h. The reaction was filtered, acidified by the addition of 3 mL of 1 N HCl and then concentrated under reduced pressure. The solid that formed was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound (195 mg, 92%) as a white solid, mp 222-230° C. Elemental Analysis for C21H14BrNO3S+0.15H2O Calc'd: C, 56.94; H, 3.25; N, 3.16. Found: C, 57.19; H, 3.18; N, 3.04.

Workup

  1. temperaturewas refluxed under nitrogen for 2.25 h
  2. filtrationThe reaction was filtered
  3. additionacidified by the addition of 3 mL of 1 N HCl
  4. concentrationconcentrated under reduced pressure
  5. customThe solid that formed
  6. filtrationwas collected by filtration
  7. washrinsed with water
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-e5b4ba1423004b18a2632ed5cdecb74c
Source dataset
uspto-grants-2009_10
Patent number
US07605172B2

Reaction notes

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