Sodium Hydroxide → 4-({[1-Bromo-6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthyl]oxy}methyl)benzoic acid

HRID 1820849Notes

Reaction equation

HRID 1820849 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]1[CH:34]=[CH:33][C:28]([C:29]([O:31]C)=[O:30])=[CH:27][CH:26]=1.[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:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[S:15][CH:16]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:23][CH2:24][C:25]1[CH:26]=[CH:27][C:28]([C:29]([OH:31])=[O:30])=[CH:33][CH:34]=1

Participants

6

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 68981175Methyl 4-({[1-bromo-6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthyl]oxy}methyl)benzoate

Product 1

HCID 115045114-({[1-Bromo-6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthyl]oxy}methyl)benzoic acidYield 73.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-({[1-bromo-6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthyl]oxy}methyl)benzoate (214.8 mg, 0.405 mmol), prepared in the previous step, and 1 N NaOH (608 μL, 0.608 mmol) in 40 mL of THF plus 40 mL of methanol plus 10 mL of water was refluxed for 24 h. By TLC starting material remained. An additional 608 μL (0.608 mmol) of 1 N NaOH was added and the mixture refluxed for 24 h. After cooling to room temperature the reaction was filtered, acidified by the addition of 5 mL of 1 N HCl and then concentrated under reduced pressure to remove the THF and methanol. The solid present was collected by filtration, washed with water and dried under reduced pressure to give the title compound (152.9 mg, 73%) as a white solid, mp 268-270° C. Elemental analysis for C27H18BrNO3S.0.20H2O Calc'd: C, 62.36; H, 3.57; N, 2.69. Found: C, 62.38; H, 3.54; N, 2.62.

Workup

  1. temperaturewas refluxed for 24 h
  2. temperaturethe mixture refluxed for 24 h
  3. filtrationwas filtered
  4. additionacidified by the addition of 5 mL of 1 N HCl
  5. concentrationconcentrated under reduced pressure
  6. customto remove the THF and methanol
  7. filtrationThe solid present was collected by filtration
  8. washwashed with water
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-4959c8f6fb13416ebb71006924bf2620
Source dataset
uspto-grants-2009_10
Patent number
US07605172B2

Reaction notes

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