Sodium Hydroxide → HCID 21392455, compound

HRID 461778Notes

Reaction equation

HRID 461778 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]([NH2:12])=[S:11])[CH2:6][CH2:5]1.[CH3:13][C:14]([C:17]([CH2:19]Br)=O)([CH3:16])[CH3:15].C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.[OH-].[Na+]>C(O)C>[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[S:11][CH:19]=[C:17]([C:14]([CH3:16])([CH3:15])[CH3:13])[N:12]=2)[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 21642BromopinacoloneHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 20514194-(2-hydroxyethyl)piperazine-1-carbothioamide

Product 1

HCID 21392455HCID 21392455, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5 g of 4-(2-hydroxyethyl)-1-piperazinyl-thiocarboxamide are added to a solution of 3.6 g of bromopinacoline in 70 cc of ethanol, and the reaction mixture is subsequently heated to the boil at reflux for 2 hours. The mixture is then concentrated by evaporation in a vacuum. The residue is dissolved in a small amount of water and is divided between chloroform and a concentrated aqueous sodium hydroxide solution. The chloroform phase is washed with water, dried over sodium sulphate and concentrated by evaporation in a vacuum. Hydrochloric acid in ethanol is added to the resulting oil and the solution is concentrated by evaporation. After recrystallizing the residue from a small amount of ethanol/diethyl ether, 2-[4-(2-hydroxyethyl)-1-piperazinyl]-4-tert.butyl-thiazole dihydrochloride, having a M.P. of 133°-142°, is obtained. The free base is obtained is known manner from the dihydrochloride by treatment with an aqueous sodium hydroxide solution.

Workup

  1. temperaturethe reaction mixture is subsequently heated to the boil
  2. temperatureat reflux for 2 hours
  3. concentrationThe mixture is then concentrated by evaporation in a vacuum
  4. dissolutionThe residue is dissolved in a small amount of water
  5. washThe chloroform phase is washed with water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated by evaporation in a vacuum
  8. additionHydrochloric acid in ethanol is added to the resulting oil
  9. concentrationthe solution is concentrated by evaporation
  10. customAfter recrystallizing the residue from a small amount of ethanol/diethyl ether, 2-[4-(2-hydroxyethyl)-1-piperazinyl]-4-tert.butyl-thiazole dihydrochloride
  11. customis obtained
  12. customThe free base is obtained

Sources & evidence

ORD record
ord-95c0f85ddc934d5ab7797455660f17e1
Source dataset
uspto-grants-1977_12
Patent number
US04064244

Reaction notes

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