Tetrahydrofuran → HCID 19862555, compound

HRID 1165150Notes

Reaction equation

HRID 1165150 reaction equation
[OH:1][C:2]1[C:14]([C:15]([CH3:18])([CH3:17])[CH3:16])=[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].[O:23]1CCC[CH2:24]1>>[CH:24]([N:7]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)[CH2:6][C:5]1[CH:13]=[C:14]([C:15]([CH3:16])([CH3:18])[CH3:17])[C:2]([OH:1])=[C:3]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:4]=1)=[O:23]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 19862543HCID 19862543, compound

Product 1

HCID 19862555HCID 19862555, compound

Procedure

15 ml of acetic anhydride and 7.5 ml of formic acid (98-100%) are mixed carefully at 0° and subsequently heated to 50° on a water-bath for 1 hour. The mixed anhydride formed is diluted with 25 ml of abs. tetrahydrofuran and 4.52 g of 1-(4-hydroxy-3,5-di-tert.-butylbenzylamino)imidazole are introduced in small portions into the solution obtained. The reaction mixture is left to stand at room temperature for 1 hour and evaporated under reduced pressure on a rotary evaporator. The residue is treated with a small amount of ice-cold water and saturated sodium bicarbonate is added up to a weakly alkaline reaction. After three-fold extraction with methylene chloride, the combined organic extracts are washed once with water and once with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue is recrystallized from ethyl acetate/n-hexane and there is obtained 1-[N-formyl-N-(4-hydroxy-3,5-di-tert.-butylbenzyl)amino]imidazole of m.p. 167°.

Workup

  1. additionis diluted with 25 ml of abs
  2. customobtained
  3. waitThe reaction mixture is left
  4. customevaporated under reduced pressure on a rotary evaporator
  5. additionThe residue is treated with a small amount of ice-cold water and saturated sodium bicarbonate
  6. additionis added up to a weakly alkaline reaction
  7. extractionAfter three-fold extraction with methylene chloride
  8. washthe combined organic extracts are washed once with water and once with saturated sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue is recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-cf67889eb171451bae1f64760a405fef
Source dataset
uspto-grants-1990_03
Patent number
US04908363

Reaction notes

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