Hydrochloric Acid → HCID 135984370, compound

HRID 1165145Notes

Reaction equation

HRID 1165145 reaction equation
[NH2:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[S:7][CH3:8].Cl.[OH:10][C:11]1[C:18]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:17][C:14]([CH:15]=O)=[CH:13][C:12]=1[C:23]([CH3:26])([CH3:25])[CH3:24]>CO>[OH:10][C:11]1[C:18]([C:19]([CH3:21])([CH3:20])[CH3:22])=[CH:17][C:14]([CH:15]=[N:1][N:2]2[CH:6]=[CH:5][N:4]=[C:3]2[S:7][CH3:8])=[CH:13][C:12]=1[C:23]([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 21782447HCID 21782447, compound

Product 1

HCID 135984370HCID 135984370, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.65 g of 1-amino-2-methylmercaptoimidazole are dissolved in 50 ml of methanol and treated with 3 ml of 2N hydrochloric acid. After the addition of 1.05 g of 4-hydroxy-3,5-di-tert.-butylbenzaldehyde, the reaction mixture is stirred at room temperature overnight. Subsequently, the solvent is removed by evaporation in a vacuum. The residue is suspended in 30 ml of water and treated with saturated sodium carbonate solution up to an alkaline reaction. The mixture is extracted three times with 20 ml of methylene chloride each time, the combined organic phases are dried over sodium sulfate, filtered and evaporated. The crystalline residue is recrystallized from water/methanol, and there is obtained 1-(4-hydroxy-3,5-di-tert.-butylbenzylideneamino)-2-methylmercaptoimidazole of m.p. 181°-183°.

Workup

  1. customSubsequently, the solvent is removed by evaporation in a vacuum
  2. additiontreated with saturated sodium carbonate solution up to an alkaline reaction
  3. extractionThe mixture is extracted three times with 20 ml of methylene chloride each time
  4. dry with materialthe combined organic phases are dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crystalline residue is recrystallized from water/methanol

Sources & evidence

ORD record
ord-9eed381bae3e4c9c874d3f97c9688e63
Source dataset
uspto-grants-1990_03
Patent number
US04908363

Reaction notes

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