Formaldehyde → Benzyl 4-(2,3,4-trihydroxybenzyl)-1-piperazinecarbodithioate

HRID 1757528Notes

Reaction equation

HRID 1757528 reaction equation
[CH2:1]=O.[N:3]1([C:9]([S:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[S:10])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[C:19]1([CH:27]=[CH:26][CH:25]=[C:23]([OH:24])[C:21]=1[OH:22])[OH:20]>C(O)C>[OH:20][C:19]1[C:21]([OH:22])=[C:23]([OH:24])[CH:25]=[CH:26][C:27]=1[CH2:1][N:6]1[CH2:7][CH2:8][N:3]([C:9]([S:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[S:10])[CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 1057PyrogallolHCID 54506580Benzyl 1-piperazinecarbodithioate

Product 1

HCID 19388519Benzyl 4-(2,3,4-trihydroxybenzyl)-1-piperazinecarbodithioateYield 93.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

To a solution of 0.51 g of 35% formalin in 7.7 ml of ethanol was added under chilling with ice a solution of 1.5 g of benzyl 1-piperazinecarbodithioate in 7.5 ml of ethanol. The mixture was stirred at room temperature for 10 min. To the mixture was further added under chilling with ice a solution of 3.7 g of pyrogallol in 15.3 ml of ethanol at once. The mixture was then stirred for 2.5 hours at room temperature. Ethanol was evaporated under reduced pressure, and the residue was extracted with dichloromethane. The dichloromethane solution was washed with water and an aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and placed under reduced pressure to distill off the solvent to give 2.17 g of the desired compound as a pale red powder, m.p. 125°-126° C. (decomp.), yield 92.9%.

Workup

  1. additionTo the mixture was further added
  2. stirringThe mixture was then stirred for 2.5 hours at room temperature
  3. customEthanol was evaporated under reduced pressure
  4. extractionthe residue was extracted with dichloromethane
  5. washThe dichloromethane solution was washed with water
  6. dry with materialan aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  7. distillationto distill off the solvent

Sources & evidence

ORD record
ord-f249c2d295104a0db22cd8cb55720889
Source dataset
uspto-grants-1995_08
Patent number
US05446146

Reaction notes

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