Formaldehyde → HCID 178441105, compound

HRID 1612594Notes

Reaction equation

HRID 1612594 reaction equation
[K].[SH:2][C:3]1[S:7][C:6](=[S:8])[N:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:4]=1.[C:15]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:20]=1[OH:29])([CH3:18])([CH3:17])[CH3:16].[CH2:30]=O.S(=O)(=O)(O)O>C(O)C>[C:25]([C:21]1[CH:22]=[C:23]([CH:24]=[C:19]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:20]=1[OH:29])[CH2:30][SH:7]1[C:3]([SH:2])=[N:4][N:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]1=[S:8])([CH3:28])([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 314052,6-Di-tert-butylphenolHCID 178528002HCID 178528002, compound

Product 1

HCID 178441105HCID 178441105, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Mercapto-3-phenyl-1,3,4-thiadiazole-2(3H) thione potassium salt (26.4 g, 0.1 mol), 2,6-di-tertbutylphenol (20.6 g, 0.1 mol), formalin (11 ml) and concentrated sulphuric acid (10 ml) in ethanol (100 ml) are heated, under reflux, for six hours. After this time, the ethanol is removed by rotary evaporation, and partitioned between ethyl acetate and water. The organic phase is dried over magnesium sulphate, filtered and the solvent removed in vacuo. A yellow oil is left (29.5 g, 66% of theory).

Workup

  1. temperatureunder reflux, for six hours
  2. customAfter this time, the ethanol is removed by rotary evaporation
  3. custompartitioned between ethyl acetate and water
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. waitA yellow oil is left (29.5 g, 66% of theory)

Sources & evidence

ORD record
ord-37d0f6bdfffd46e1a9f5dc2a2cb8a15d
Source dataset
uspto-grants-1993_03
Patent number
US05190723

Reaction notes

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