Formaldehyde → HCID 19388491, compound

HRID 1460174Notes

Reaction equation

HRID 1460174 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.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:22]=[O:23])[CH:18]=[CH:19][C:20]=1[OH:21]>C(O)C>[CH:22]([C:17]1[CH:16]=[C:15]([O:14][CH3:13])[C:20]([OH:21])=[C:19]([CH:18]=1)[CH2:1][N:6]1[CH2:7][CH2:8][N:3]([C:9]([S:11][CH3:12])=[S:10])[CH2:4][CH2:5]1)=[O:23]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 1183VanillinHCID 21278808Methyl piperazine-1-carbodithioate

Product 1

HCID 19388491HCID 19388491, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

In 10 ml of ethanol was dissolved 0.86 g of 35% formalin. To the solution was dropwise added under chilling with ice a solution of 1.94 g of methyl 1-piperazinecarbodithioate in 4 ml of ethanol. The mixture was then stirred for 30 min. at room temperature. Under chilling with ice, a solution of 1.52 g of vanilline in 4 ml of ethanol was added to the reaction mixture. The mixture was stirred for 40 min. at room temperature and then refluxed under heating for 10 hours. The reaction mixture was cooled to room temperature to precipitate crystals. The crystals were collected and washed with ethanol to give 2.58 g of the desired compound as a white crystalline product, m.p. 144°-145° C. (decomp.), yield 75.8%.

Workup

  1. additionTo the solution was dropwise added
  2. temperatureUnder chilling with ice
  3. stirringThe mixture was stirred for 40 min. at room temperature
  4. temperaturerefluxed
  5. temperatureunder heating for 10 hours
  6. temperatureThe reaction mixture was cooled to room temperature
  7. customto precipitate crystals
  8. customThe crystals were collected
  9. washwashed with ethanol

Sources & evidence

ORD record
ord-027b461efa454be9b9f3b7f6a57dc4e5
Source dataset
uspto-grants-1991_12
Patent number
US05070089

Reaction notes

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