Benzoyl isothiocyanate → N-Benzoyl-N'-[2-hydroxy-3-[3-(1-piperidinylmethyl)phenoxy]propyl]-1,3,4-thiadiazole-2,5-diamine

HRID 4629

Reaction equation

HRID 4629 reaction equation
[C:1]([N:9]=[C:10]=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:12][CH:13]([CH2:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[CH:23]=1)[CH2:14][NH:15][C:16]([NH:18][NH2:19])=S>C1COCC1>[C:1]([NH:9][C:10]1[S:11][C:16]([NH:15][CH2:14][CH:13]([OH:12])[CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][N:29]3[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)[CH:23]=2)=[N:18][N:19]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 13657332N-[2-hydroxy-3-[3-(1-piperidinylmethyl)phenoxy]propyl]-hydrazine carbothioamide

Product 1

HCID 13657364N-Benzoyl-N'-[2-hydroxy-3-[3-(1-piperidinylmethyl)phenoxy]propyl]-1,3,4-thiadiazole-2,5-diamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.33 g (2 mmol) of benzoyl isothiocyanate are added to 0.68 g (2 mmol) of N-[2-hydroxy-3-[3-(1-piperidinylmethyl)phenoxy]propyl]-hydrazine carbothioamide in 20 ml of THF and the reaction mixture is stirred overnight at room temperature. After removal of the THF by evaporation, the solid residue is washed with ether and dissolved in 30 ml of ethanol with heating, and 1 ml of 30% hydrogen peroxide is added. The sulphur which separates is filtered off, the filtrate is concentrated by evaporation and the oily residue is purified by preparative layer chromotography.

Workup

  1. customAfter removal of the THF
  2. customby evaporation
  3. washthe solid residue is washed with ether
  4. dissolutiondissolved in 30 ml of ethanol
  5. temperaturewith heating
  6. addition1 ml of 30% hydrogen peroxide is added
  7. filtrationThe sulphur which separates is filtered off
  8. concentrationthe filtrate is concentrated by evaporation
  9. customthe oily residue is purified by preparative layer chromotography

Sources & evidence

ORD record
ord-9e8a6fca991c4f188febdba8ae9ce0c8
Source dataset
uspto-grants-1988_02
Patent number
US04727081

Linked notes

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