Water → HCID 22595113, compound

HRID 1761291Notes

Reaction equation

HRID 1761291 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH2:8].[C:9]([C:13]1[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:18]=[C:15]([CH:16]=O)[C:14]=1[OH:25])([CH3:12])([CH3:11])[CH3:10].[OH2:26]>C(O)C>[C:9]([C:13]1[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:18]=[C:15]([CH2:16][NH:1][CH:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]2[NH:8][CH2:16][C:15]2[C:18](=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:20]=[C:13]([C:9]([CH3:11])([CH3:10])[CH3:12])[CH:14]=2)[OH:26])[C:14]=1[OH:25])([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 438061,2-Diaminocyclohexane, trans-HCID 6880233,5-Di-tert-butylsalicylaldehyde

Product 1

HCID 22595113HCID 22595113, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Rac-trans-1,2-diaminocyclohexane (6.09 g, 53 mmol) was dissolved in 300 ml of ethanol and placed in a three-necked flask fitted with a mechanical stirrer. 3,5-Di-tert-butylsalicylaldehyde (25.0 g, 107 mmol) was then added. The mixture was subsequently refluxed for one hour, forming a red suspention. After cooling, about 100 ml of water were added dropwise while stirring. The precipitate formed was filtered off and washed with a small portion of 95% strength ethanol, giving 29.8 g of crude product. This was purified by recrystallizing it once from 350 ml of ethanol. This gave 27.18 g of pure product as a yellow powder. The yield was 94%.

Workup

  1. customplaced in a three-necked flask
  2. customfitted with a mechanical stirrer
  3. temperatureThe mixture was subsequently refluxed for one hour
  4. customforming a red suspention
  5. temperatureAfter cooling
  6. customThe precipitate formed
  7. filtrationwas filtered off
  8. washwashed with a small portion of 95% strength ethanol

Sources & evidence

ORD record
ord-86a1daad180c4c2186cf7d691055d480
Source dataset
uspto-grants-2005_01
Patent number
US06846961B2

Reaction notes

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