Ammonia → HCID 19862543, compound

HRID 1165147Notes

Reaction equation

HRID 1165147 reaction equation
[OH:1][C:2]1[C:16]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:15][C:5]([CH2:6][NH:7][N:8]2[CH:12]=[CH:11][N:10]=[C:9]2SC)=[CH:4][C:3]=1[C:21]([CH3:24])([CH3:23])[CH3:22].[BH4-].[Na+].N>C(O)C.[Ni](Cl)Cl>[OH:1][C:2]1[C:16]([C:17]([CH3:19])([CH3:18])[CH3:20])=[CH:15][C:5]([CH2:6][NH:7][N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[CH:4][C:3]=1[C:21]([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 4311764Sodium borohydrideHCID 56613324HCID 56613324, compound

Product 1

HCID 19862543HCID 19862543, compound

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 702EthanolSolvent

Procedure

Variant (a): 200 mg of 1-(4-hydroxy-3,5-di-tert.-butylbenzylamino)-2-methylmercaptoimidazole are dissolved in 8 ml of ethanol together with 0.41 g of nickel(II) chloride.6H2O. This solution is cooled in an ice-bath and 0.7 g of sodium borohydride is added portionwise within 1 hour. After completion of the addition, the ice-bath is removed and the black reaction mixture is stirred at room temperature for an additional 4 hours. For the work-up, the mixture is again cooled and sufficient 2N hydrochloric acid is added so that the reaction mixture has an acidic reaction. The resulting mixture is stirred for a few minutes and treated with conc. ammonia up to an alkaline reaction. Subsequently, the mixture is filtered through a bed of siliceous earth and the filter cake is washed five times with methylene chloride. The organic phase of the filtrate is separated, washed twice with water, dried over sodium sulfate and evaporated. The crystalline residue is reprecipitated from methanol/water and there is obtained 1-(4-hydroxy-3,5-di-tert.-butylbenzylamino)imidazole in the form of colorless crystals of m.p. 171°-174°.

Workup

  1. temperatureThis solution is cooled in an ice-bath
  2. additionAfter completion of the addition
  3. customthe ice-bath is removed
  4. temperatureFor the work-up, the mixture is again cooled
  5. additionsufficient 2N hydrochloric acid is added so that the reaction mixture
  6. customan acidic reaction
  7. stirringThe resulting mixture is stirred for a few minutes
  8. filtrationSubsequently, the mixture is filtered through a bed of siliceous earth
  9. washthe filter cake is washed five times with methylene chloride
  10. customThe organic phase of the filtrate is separated
  11. washwashed twice with water
  12. dry with materialdried over sodium sulfate
  13. customevaporated
  14. customThe crystalline residue is reprecipitated from methanol/water

Sources & evidence

ORD record
ord-d80ccf4a54a64753b10b88f4125c8340
Source dataset
uspto-grants-1990_03
Patent number
US04908363

Reaction notes

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