Sodium Hydroxide → HCID 178467457, Verbindung

HRID 542385Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 542385
[CH3:1][N:2]([CH3:17])[C:3]1[C:8]([NH:9][C:10](=[O:13])[CH2:11][Cl:12])=[C:7]([O:14][CH2:15][CH3:16])[N:6]=[CH:5][N:4]=1.Cl.[NH:19]1[CH:23]=[CH:22][C:21]([CH2:24]Cl)=[N:20]1.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl.O>[NH:19]1[CH:23]=[CH:22][C:21]([CH2:24][N:9]([C:8]2[C:3]([N:2]([CH3:17])[CH3:1])=[N:4][CH:5]=[N:6][C:7]=2[O:14][CH2:15][CH3:16])[C:10](=[O:13])[CH2:11][Cl:12])=[N:20]1

Komponenten

7

Edukt 3

HCID 14798Sodium HydroxideHCID 20208140N-(4-dimethylamino-6-ethoxypyrimidin-5-yl)-chloroacetamideHCID 178478564HCID 178478564, Verbindung

Produkt 1

HCID 178467457HCID 178467457, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 12.9 g (0.05 mol) N-(4-dimethylamino-6-ethoxypyrimidin-5-yl)-chloroacetamide and 2 g benzyltriethylammoniumchloride in 150 g of CH2Cl2 are added 8.4 g (0.055 mol) of 1-pyrazolylmethylchloride-hydrochloride. To this mixture are quickly added 25 ml of 40% NaOH, whereby the temperature rises from 18° to 32°. The mixture is then stirred for 2 hours and diluted with water. The organic phase is separated off and dried over Na2SO4. The dried solution is evaporated to give an orange oil that is chromatographed on silica gel with the aid of ethylacetate. The thus obtained yellow oil is dissolved in diethylether and crystallised in a deep-freezer. The title compound is obtained in the form of white crystals of m.p. 112°-114°.

Aufarbeitung

  1. customrises from 18° to 32°
  2. customThe organic phase is separated off
  3. dry with materialdried over Na2SO4
  4. customThe dried solution is evaporated
  5. customto give an orange oil that
  6. customis chromatographed on silica gel with the aid of ethylacetate
  7. dissolutionThe thus obtained yellow oil is dissolved in diethylether
  8. customcrystallised in a deep-freezer

Quellen und Nachweise

ORD-Eintrag
ord-ef3746e0b2784720a0954597e16b8c31
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04657579

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