Potassium Hydroxide → HCID 20553731, compound

HRID 1106237Notes

Reaction equation

HRID 1106237 reaction equation
[C:1]1([S:7]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([CH2:18]Cl)=O)=[CH:11][CH:10]=2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N:22]1[CH2:27][CH2:26][N:25]([C:28](=[S:30])[NH2:29])[CH2:24][CH2:23]1)=O.[OH-].[K+]>C(O)C.O>[C:1]1([S:7]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]3[N:29]=[C:28]([N:25]4[CH2:26][CH2:27][NH:22][CH2:23][CH2:24]4)[S:30][CH:18]=3)=[CH:11][CH:10]=2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 186230804-Formylpiperazine-1-carbothioamideHCID 20553734HCID 20553734, compound

Product 1

HCID 20553731HCID 20553731, compoundYield 83.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 14.6 g of 1-(4-phenylsulfinylphenyl)-3-chloroacetone and 8.7 g of 1-formyl-4-thiocarbamoyl piperazine, melting (Kofler) at 228° C., in 250 ml of ethanol at 90%, was boiled for one hour. There was added to the hot solution a solution of 9.3 g of KOH at 85% in 10 ml of water, and the mixture was refluxed for three hours, in order to hydrolyze the formyl protecting group. Then the solvent was evaporated off under reduced pressure, and the oily residue was taken up with 200 ml of a N hydrochloric acid solution. The insoluble matter was extracted with ether. The acid solution was alkalized with K2CO3, and the resulting base was extracted thrice with, each time, 50 ml of chloroform. The chloroform part was washed with water, then the solvent was evaporated off. There was obtained 16 g of 1-[4-(4-phenylsulfinylbenzyl)-2-thiazolyl]piperazine, as raw base, M.P. of its dihydrochloride: 158°-160° C.

Workup

  1. customat 228° C.
  2. temperaturethe mixture was refluxed for three hours, in order
  3. customThen the solvent was evaporated off under reduced pressure
  4. extractionThe insoluble matter was extracted with ether
  5. extractionthe resulting base was extracted thrice with, each time, 50 ml of chloroform
  6. washThe chloroform part was washed with water
  7. customthe solvent was evaporated off

Sources & evidence

ORD record
ord-cd31496629c64d76b745d69025094ef6
Source dataset
uspto-grants-1982_01
Patent number
US04312869

Reaction notes

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