Sodium cyanoborohydride → HCID 19862543, compound

HRID 1165141Notes

Reaction equation

HRID 1165141 reaction equation
[OH:1][C:2]1[C:14]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:13][C:5]([CH:6]=[N:7][N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[CH:4][C:3]=1[C:19]([CH3:22])([CH3:21])[CH3:20].C([BH3-])#N.[Na+]>C(O)(=O)C>[OH:1][C:2]1[C:14]([C:15]([CH3:17])([CH3:16])[CH3:18])=[CH:13][C:5]([CH2:6][NH:7][N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[CH:4][C:3]=1[C:19]([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 135973970HCID 135973970, compound

Product 1

HCID 19862543HCID 19862543, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.9 g of 1-(4-hydroxy-3,5-di-tert.-butylbenzylideneamino)imidazole are suspended in 10 ml of glacial acetic acid and treated with 1.61 g of sodium cyanoborohydride, whereby a solution results. The solution is stirred at room temperature overnight and then evaporated in a vacuum. The residue is treated with 10 ml of water, neutralized (pH=7) with ice-cold saturated sodium bicarbonate solution and extracted three times with 30 ml of methylene chloride each time. The combined organic phases are dried over sodium sulfate, filtered and evaporated in a vacuum. The residue is crystallized with ehter. The product is removed by filtration and reprecipitated from ethanol/water. There is obtained 1-(4-hydroxy-3,5-di-tert.-butylbenzylamino)imidazole of m.p. 171°-174°.

Workup

  1. customresults
  2. customevaporated in a vacuum
  3. additionThe residue is treated with 10 ml of water
  4. extractionextracted three times with 30 ml of methylene chloride each time
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in a vacuum
  8. customThe residue is crystallized with ehter
  9. customThe product is removed by filtration
  10. customreprecipitated from ethanol/water

Sources & evidence

ORD record
ord-42081a6a0aab4457801a1309febb7be1
Source dataset
uspto-grants-1990_03
Patent number
US04908363

Reaction notes

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