Sodium Hydroxide → HCID 11719225, compound

HRID 1820847Notes

Reaction equation

HRID 1820847 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:3]=1[CH2:4][C:5]1[S:6][CH:7]=[C:8]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]=[C:15]([O:20][CH2:21][C:22]([O:24]C)=[O:23])[CH:14]=[CH:13]3)[N:9]=1.[OH-].[Na+]>C1COCC1.CO.O>[Cl:30][C:26]1[CH:27]=[CH:28][CH:29]=[C:2]([Cl:1])[C:3]=1[CH2:4][C:5]1[S:6][CH:7]=[C:8]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]=[C:15]([O:20][CH2:21][C:22]([OH:24])=[O:23])[CH:14]=[CH:13]3)[N:9]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 86603573HCID 86603573, compound

Product 1

HCID 11719225HCID 11719225, compoundYield 75.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl ({6-[2-(2,6-dichlorobenzyl)-1,3-thiazol-4-yl]-2-naphthyl}oxy)acetate (205 mg, 0.447 mmol), prepared in the previous step, and 1 N NaOH (671 μL, 0.671 mmol) in 20 mL of THF plus 20 mL of methanol plus 10 mL of water was refluxed under nitrogen for 2.5 h. The reaction was filtered, acidified by the addition of 3 mL of 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 (150 mg, 74%) as an off-white solid, mp 205-207° C. Elemental Analysis for C22H15Cl2NO3S+0.30H2O Calc'd: C, 58.75; H, 3.50; N, 3.11. Found: C, 59.09; H, 3.58; N, 2.92.

Workup

  1. temperaturewas refluxed under nitrogen for 2.5 h
  2. filtrationThe reaction was filtered
  3. additionacidified by the addition of 3 mL of 1 N HCl
  4. concentrationconcentrated under reduced pressure
  5. customto remove the THF and methanol
  6. filtrationThe solid present was collected by filtration
  7. washrinsed with water
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-a1c8ae5dd7fc488a83e33258bb83fb6c
Source dataset
uspto-grants-2009_10
Patent number
US07605172B2

Reaction notes

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