Water → N'-(4-tert-butyl-benzyl)-N-ethyl-N-m-tolyl-ethane-1,2-diamine

HRID 855238

Reaktionsgleichung

Reaktionsgleichung von HRID 855238
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:13]([N:15]([C:19]1[CH:20]=[C:21]([CH3:25])[CH:22]=[CH:23][CH:24]=1)[CH2:16][CH2:17][NH2:18])[CH3:14].[BH4-].[Na+].O>CO>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH:18][CH2:17][CH2:16][N:15]([CH2:13][CH3:14])[C:19]2[CH:20]=[C:21]([CH3:25])[CH:22]=[CH:23][CH:24]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 703244-tert-ButylbenzaldehydeHCID 879841,2-Ethanediamine, N1-ethyl-N1-(3-methylphenyl)-HCID 4311764Sodium borohydride

Produkt 1

HCID 69342865N'-(4-tert-butyl-benzyl)-N-ethyl-N-m-tolyl-ethane-1,2-diamineAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

1.62 g (10 mmol) of 4-tert-butyl benzaldehyde and 1.78 g (10 mmol) of N*1*-ethyl-N*1* -m-tolyl-ethane-1,2-diamine were dissolved in 20 ml methanol and the solution was stirred for 2 h at rt. 567 mg (15 mmol) of sodium borohydride were added in portions under nitrogen. The reaction mixture was stirred at rt over night. Water was added and the solvent was evaporated. The reaction mixture was extracted with diethyl ether and the organic layer was washed with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and the solvent was evaporated to leave the 3.08 g (95%) product as a light yellow oil. 1H NMR (DMSO-d6, 300 MHz): δ 7.33 (d, 2H), 7.24 (d, 2H), 7.09 (dd, 1H), 6.51 (m, 3H), 3.78 (s, 2H), 3.42 (t, 2H), 3.34 (q, 2H), 2.85 (t, 2H), 2.29 (s, 3H), 1.31 (s, 9H), 1.11 (t, 3H).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at rt over night
  2. customthe solvent was evaporated
  3. extractionThe reaction mixture was extracted with diethyl ether
  4. washthe organic layer was washed with saturated aqueous NaCl solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-f8163ec0f6c446e3a9d9efb6fbe68099
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259183B2

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