N-Ethylaniline → HCID 24946957, compound

HRID 2043321Notes

Reaction equation

HRID 2043321 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].[CH:10]([C:12]1[N:13]=[CH:14][NH:15][CH:16]=1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl.C(O)(=O)C.C(OCC)(=O)C>[CH2:1]([N:3]([CH2:10][C:12]1[NH:13][CH:14]=[N:15][CH:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2]

Participants

8

Reactant 4

HCID 7670N-EthylanilineHCID 764281H-Imidazole-4-carbaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 24946957HCID 24946957, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-ethylaniline (0.145 g, 1.2 mmol) in 1,2-dichloroethane (5 ml) were added molecular sieves (2 g, size 0.4 nM) and 4-formylimidazole (0.3 g, 3.12 mmol). After stirring the mixture for 5 min at room temperature sodium triacetoxyborohydride (1.02 g, 4.8 mmol) and acetic acid (5 drops) were added. The reaction mixture was stirred at room temperature overnight. For workup ethyl acetate (50 ml) and 1 M sodium bicarbonate solution (30 ml) were added and the mixture was shaken. The organic layer was separated, dried over magnesium sulfate and evaporated. The residue was purified using flash chromatography (column: Isolute® Flash-NH2 (Separtis); eluent: ethyl acetate/methanol=95:5) to yield a white solid (122 mg, 51%); MS (ISP): 202.0 ((M+H)+.).

Workup

  1. additionwere added
  2. stirringthe mixture was shaken
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified

Sources & evidence

ORD record
ord-3612db451a304aa6bcc12d2fc33ead98
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Reaction notes

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