Potassium Hydroxide → 4-(2-(Aminomethyl)-1,3-thiazol-4-yl)-2,6-di(tert-butyl)phenol

HRID 2065963Notes

Reaction equation

HRID 2065963 reaction equation
[OH-].[K+].[C:3]([C:7]1[CH:8]=[C:9]([C:18]2[N:19]=[C:20]([CH2:23][NH:24]C(=O)OCC3C=CC=CC=3)[S:21][CH:22]=2)[CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])([CH3:6])([CH3:5])[CH3:4]>CO>[NH2:24][CH2:23][C:20]1[S:21][CH:22]=[C:18]([C:9]2[CH:10]=[C:11]([C:14]([CH3:15])([CH3:16])[CH3:17])[C:12]([OH:13])=[C:7]([C:3]([CH3:6])([CH3:5])[CH3:4])[CH:8]=2)[N:19]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 9803928HCID 9803928, compound

Product 1

HCID 99050904-(2-(Aminomethyl)-1,3-thiazol-4-yl)-2,6-di(tert-butyl)phenolYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.1 ml of a 40% solution of potassium hydroxide is added dropwise to a solution of 0.106 g (1.1 mmol) of the compound of Example 10 in 10 ml of methanol. After overnight stirring under reflux, the reaction mixture is concentrated under vacuum and the residue is diluted with dichloromethane and washed with a 1N solution of HCl then with 50 ml of a saturated solution of NaCl. The organic phase is separated and dried over magnesium sulphate, filtered and concentrated under vacuum. The expected product is obtained after chromatography on a silica column (eluent: 5% ethanol in dichloromethane) in the form of a brown foam with a yield of 76%.

Workup

  1. temperatureunder reflux
  2. concentrationthe reaction mixture is concentrated under vacuum
  3. additionthe residue is diluted with dichloromethane
  4. washwashed with a 1N solution of HCl
  5. customThe organic phase is separated
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9028da00da8e464fa2c2750e6e21ba14
Source dataset
uspto-grants-2012_10
Patent number
US08288560B2

Reaction notes

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