Bromopinacolone → HCID 21392477, compound

HRID 461780Notes

Reaction equation

HRID 461780 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([NH2:12])=[S:11])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].[CH3:13][C:14]([C:17]([CH2:19]Br)=O)([CH3:16])[CH3:15]>C(O)C>[CH2:1]([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)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 21642BromopinacoloneHCID 47405064-prop-2-enylpiperazine-1-carbothioamide

Product 1

HCID 21392477HCID 21392477, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.7 g of 4-allyl-1-piperazinyl-thiocarboxamide are added to a solution of 3.6 g of bromopinacoline in 40 cc of ethanol, and the reaction mixture is subsequently heated to the boil at reflux for 2 hours. The mixture is subsequently concentrated by evaporation in a vacuum, the residue is dissolved in a small amount of water and divided between ether and a concentrated aqueous sodium hydroxide solution. The ether phase is washed with water, dried over sodium sulphate and saturated with hydrogen chloride gas after filtration. The monohydrochloride of 2-(4-allyl-1-piperazinyl)-4-tert.butyl-thiazole crystallizes and has an M.P. of 212°-214° after recrystallization from ethanol/diisopropyl ether.

Workup

  1. temperaturethe reaction mixture is subsequently heated to the boil
  2. temperatureat reflux for 2 hours
  3. concentrationThe mixture is subsequently concentrated by evaporation in a vacuum
  4. dissolutionthe residue is dissolved in a small amount of water
  5. washThe ether phase is washed with water
  6. dry with materialdried over sodium sulphate and saturated with hydrogen chloride gas
  7. filtrationafter filtration
  8. customThe monohydrochloride of 2-(4-allyl-1-piperazinyl)-4-tert.butyl-thiazole crystallizes
  9. customafter recrystallization from ethanol/diisopropyl ether

Sources & evidence

ORD record
ord-aeffb55f95fd41658204d7f3c3b97d7a
Source dataset
uspto-grants-1977_12
Patent number
US04064244

Reaction notes

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