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

HRID 2421264Notes

Reaction equation

HRID 2421264 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-fa324ad7d8fb41ecbbf165b44d096c76
Source dataset
uspto-grants-2011_06
Patent number
US07956075B2

Reaction notes

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