Benzaldehyde → Bis(4-(2-benzalaminoethyl)piperazine-1-thiocarbonyl) Disulfane

HRID 1032000Notes

Reaction equation

HRID 1032000 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.[C:18](=[S:20])=[S:19]>[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[K+].[K+].[K+].[Fe+3].C(N(CC)CC)C.C(O)C.O>[CH:1](=[N:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][N:15]([C:18]([S:20][S:20][C:18]([N:15]2[CH2:16][CH2:17][N:12]([CH2:11][CH2:10][N:9]=[CH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:13][CH2:14]2)=[S:19])=[S:19])[CH2:14][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 240BenzaldehydeHCID 6348Carbon DisulfideHCID 8795Aminoethylpiperazine

Product 1

HCID 86744207Bis(4-(2-benzalaminoethyl)piperazine-1-thiocarbonyl) Disulfane

Reagents, catalysts & solvents 4

HCID 26250Potassium ferricyanideCatalystHCID 702EthanolSolvent2×HCID 962WaterSolvent2×HCID 8471TriethylamineSolvent

Procedure

10.6 parts of benzaldehyde are added to a solution of 12.9 parts of 1-(2-aminoethyl)piperazine in 24 parts of water and 24 parts of ethanol. 7.6 parts of carbon disulfide are then slowly added dropwise with ice cooling, whereby a precipitate forms. This is again dissolved after dilution with 100 parts each of water and of ethanol by addition of 10.1 parts of triethylamine and oxidized with 33 parts with potassium hexacyanoferrate(III). The product that now precipitates is filtered, washed repeatedly with water and finally with methanol, and dried at 30° C. in vacuum. Obtained are 26 parts of a substance with 56.4% C, 6.3% H, 14.5% N, and 21.5% S (calculated: 57.5% C, 6.2% H, 14.4% N, 21.9% S), which corresponds to the title compound of this Example according to IR and 1H-NMR.

Workup

  1. customThe product that now precipitates
  2. filtrationis filtered
  3. washwashed repeatedly with water and finally with methanol
  4. customdried at 30° C. in vacuum
  5. customObtained

Sources & evidence

ORD record
ord-d248eaf8c8f946bf876c71d1d6e3a01d
Source dataset
uspto-grants-1990_09
Patent number
US04956433

Reaction notes

Loading…