Sodium cyanoborohydride → HCID 56613324, compound

HRID 1165146Notes

Reaction equation

HRID 1165146 reaction equation
[OH:1][C:2]1[C:16]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:15][C:5]([CH:6]=[N:7][N:8]2[CH:12]=[CH:11][N:10]=[C:9]2[S:13][CH3:14])=[CH:4][C:3]=1[C:21]([CH3:24])([CH3:23])[CH3:22].C([BH3-])#N.[Na+]>C(O)(=O)C>[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]=[C:9]2[S:13][CH3:14])=[CH:4][C:3]=1[C:21]([CH3:24])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 135984370HCID 135984370, compound

Product 1

HCID 56613324HCID 56613324, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.04 g of 1-(4-hydroxy-3,5-di-tert.-butylbenzylideneamino)-2-methylmercaptoimidazole are dissolved in 20 ml of glacial acetic acid and treated portionwise within 30 minutes with 0.43 g of 90% sodium cyanoborohydride. The reaction mixture is stirred at room temperature overnight, whereupon the solvent is removed by evaporation in a vacuum and the residue is taken up with 20 ml of water. Saturated sodium carbonate solution is added up to an alkaline reaction and the mixture is extracted three times with 15 ml of methylene chloride each time. The combined organic phases are dried over sodium sulfate, filtered and evaporated. The residue is recrystallized from methanol/water and there is obtained 1-(4-hydroxy-3,5-di-tert.-butylbenzylamino)-2-methylmercaptoimidazole of m.p. 110°-113°.

Workup

  1. customis removed by evaporation in a vacuum
  2. additionSaturated sodium carbonate solution is added up to an alkaline reaction
  3. extractionthe mixture is extracted three times with 15 ml of methylene chloride each time
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is recrystallized from methanol/water

Sources & evidence

ORD record
ord-017a309b2b7441e5850e0ff7a86b171e
Source dataset
uspto-grants-1990_03
Patent number
US04908363

Reaction notes

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