Formaldehyde → 3-(Dimethylamino)-2-methyl-1-(3-nitro-phenyl)-propan-1-one

HRID 1026781

Reaktionsgleichung

Reaktionsgleichung von HRID 1026781
Cl.[CH3:2][NH:3][CH3:4].C=O.[C:7](OC(=O)C)(=O)C.[N+:14]([C:17]1[CH:18]=[C:19]([C:23](=[O:26])[CH2:24][CH3:25])[CH:20]=[CH:21][CH:22]=1)([O-:16])=[O:15].[OH-].[Na+]>O.C(OC)(C)(C)C>[CH3:2][N:3]([CH3:7])[CH2:4][CH:24]([CH3:25])[C:23]([C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([N+:14]([O-:16])=[O:15])[CH:18]=1)=[O:26]

Komponenten

8

Edukt 5

HCID 712FormaldehydeHCID 7918Acetic Anhydride3×HCID 10473Dimethylamine, hydrochlorideHCID 14798Sodium HydroxideHCID 870963'-Nitropropiophenone

Produkt 1

HCID 672453313-(Dimethylamino)-2-methyl-1-(3-nitro-phenyl)-propan-1-oneAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 15413tert-Butyl methyl etherLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

N,N-dimethylamine HCl (80.0 g, 0.982 mol), paraformaldehyde (45 g, 1.499 mol), water (30 g, 1.667 mol) and acetic anhydride (30 ml/32.4 g, 0.32 mol) are added into a 1 liter four-neck flask, provided with mechanical stirrer, thermometer and dropping funnel. The suspension is slowly heated up to 50° C. and stirred for 30 minutes. Then, acetic anhydride (200 ml/216 g, 2.12 mol) is dripped thereinto slowly and portionwise. The reaction mixture is stirred at 50-70° C. for at least 1 hour then 1-(3-nitrophenyl)propan-1-one (150 g, 0.837 mol) and acetic anhydride (200 ml/216 g, 2.12 mol) suspension is added. The reaction mixture is stirred at about 70° C. for 16 hours, then conversion is monitored using HPLC. When the conversion is >90% about 200 ml of solvent are distilled under vacuum and 600 ml of ethanol are added. The obtained suspension is cooled to 20-25° C. and allowed to stir for 3 hours. Then it is filtered and washed with 300 ml of acetone. About 210 g of almost colourless solid and with HPLC purity >99% are obtained. The wet product is suspended in water (600 ml), t-butyl-methylether (600 ml) and the pH is adjusted to 10-12 with 28% sodium hydroxide. The two phases are stirred for about 30 minutes then they are separated. The organic phase is concentrated to oily residue. About 182 g of slightly yellowish oil (about 92% yield) with HPLC purity >99% are obtained.

Aufarbeitung

  1. customprovided with mechanical stirrer
  2. stirringThe reaction mixture is stirred at 50-70° C. for at least 1 hour
  3. stirringThe reaction mixture is stirred at about 70° C. for 16 hours
  4. distillationare distilled under vacuum and 600 ml of ethanol
  5. additionare added
  6. temperatureThe obtained suspension is cooled to 20-25° C.
  7. stirringto stir for 3 hours
  8. filtrationThen it is filtered
  9. washwashed with 300 ml of acetone
  10. customAbout 210 g of almost colourless solid and with HPLC purity >99% are obtained
  11. stirringThe two phases are stirred for about 30 minutes
  12. customthey are separated
  13. concentrationThe organic phase is concentrated to oily residue

Quellen und Nachweise

ORD-Eintrag
ord-e5f5cc4dc42f42e5a0fd80f868279363
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729308B2

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