Formaldehyde → Methyl 4-(6-propyloxycarbonyl-2,3,4-trihydroxybenzyl)-1-piperazinecarbodithioate

HRID 1757535

Reaction equation

HRID 1757535 reaction equation
[CH2:1]=O.[N:3]1([C:9]([S:11][CH3:12])=[S:10])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[C:13]([O:24][CH2:25][CH2:26][CH3:27])(=[O:23])[C:14]1[CH:22]=[C:20]([OH:21])[C:18]([OH:19])=[C:16]([OH:17])[CH:15]=1>C(O)C>[CH2:25]([O:24][C:13]([C:14]1[C:15]([CH2:1][N:6]2[CH2:7][CH2:8][N:3]([C:9]([S:11][CH3:12])=[S:10])[CH2:4][CH2:5]2)=[C:16]([OH:17])[C:18]([OH:19])=[C:20]([OH:21])[CH:22]=1)=[O:23])[CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 4947Propyl GallateHCID 21278808Methyl piperazine-1-carbodithioate

Product 1

HCID 53992097Methyl 4-(6-propyloxycarbonyl-2,3,4-trihydroxybenzyl)-1-piperazinecarbodithioateYield 46.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

In 10 ml of ethanol was dissolved 0.86 g (10 mmol.) of 35% formalin. To thesolution placed in an ice bath was further added a solution of 1.94 g (10 mmol., purity 90.7%) of methyl 1-piperazinecarbodithioate in 4 ml of ethanol. The resulting mixture was then stirred for 30 min. at room temperature. To the mixture placed in an ice bath was dropwise added a solution of 2.12 g (10 mmol.) of propyl gallate in 4 ml of ethanol. The mixture was stirred overnight at room temperature and subsequently refluxed under heating for 4 hours. The mixture was cooled to room temperature. Precipitated crystals were collected by filtration and washedwith ethanol to give 1.848 g of the desired compound as a grayish powder, m.p. 142°-144° C. (decomp.), yield 31.3%.

Workup

  1. customTo thesolution placed in an ice bath
  2. customTo the mixture placed in an ice bath
  3. stirringThe mixture was stirred overnight at room temperature
  4. temperaturesubsequently refluxed
  5. temperatureunder heating for 4 hours
  6. temperatureThe mixture was cooled to room temperature
  7. customPrecipitated crystals
  8. filtrationwere collected by filtration and washedwith ethanol

Sources & evidence

ORD record
ord-add8c06a27be4b73877e44f6eb09ab5a
Source dataset
uspto-grants-1995_08
Patent number
US05446146

Linked notes

Loading…