Sodium Hydroxide → N-benzyl-6-chloro-N-(2,2,2-trifluoroethyl)pyrimidine-4-carboxamide

HRID 74528

Reaktionsgleichung

Reaktionsgleichung von HRID 74528
[CH2:1]([NH:8][CH2:9][C:10]([F:13])([F:12])[F:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[Cl:16][C:17]1[N:22]=[CH:21][N:20]=[C:19]([C:23](Cl)=[O:24])[CH:18]=1.C(=O)([O-])O.[Na+]>ClCCl>[CH2:1]([N:8]([CH2:9][C:10]([F:12])([F:11])[F:13])[C:23]([C:19]1[CH:18]=[C:17]([Cl:16])[N:22]=[CH:21][N:20]=1)=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 4962181Benzyl-(2,2,2-trifluoro-ethyl)-amineHCID 184220986-Chloropyrimidine-4-carbonyl chloride

Produkt 1

HCID 58117522N-benzyl-6-chloro-N-(2,2,2-trifluoroethyl)pyrimidine-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1.04 g (5.50 mmol) benzyl-(2,2,2-trifluorethyl)-amine and 5.50 mL (5.50 mmol) of a 1M sodium hydroxide solution were added dropwise while cooling with a bath of ice/ethanol to 1.00 g (5.65 mmol) 6-chloropyrimidine-4-carboxylic acid chloride in 20 mL dichloromethane. The mixture was first stirred for 2 h while being cooled and then for a further 1 h at RT. 50 mL of a saturated sodium hydrogen carbonate solution were added and the mixture was stirred for 10 min. The organic phase was separated off, washed with water (1×30 mL) and 1M hydrochloric acid (1×50 mL), dried on sodium sulphate, filtered and evaporated down i. vac. The product was reacted further without any further purification.

Aufarbeitung

  1. temperaturewhile being cooled
  2. waitfor a further 1 h at RT
  3. stirringthe mixture was stirred for 10 min
  4. customThe organic phase was separated off
  5. washwashed with water (1×30 mL) and 1M hydrochloric acid (1×50 mL)
  6. customdried on sodium sulphate
  7. filtrationfiltered
  8. customevaporated down i
  9. customThe product was reacted further without any further purification

Quellen und Nachweise

ORD-Eintrag
ord-85f255f912d74627b1b16b998fbcf446
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829006B2

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