Sodium Hydroxide → [4-(4-Chloro-phenyl)-pyrimidin-2-yl]-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-amine

HRID 976265

Reaktionsgleichung

Reaktionsgleichung von HRID 976265
[N+]([O-])(O)=O.[F:5][C:6]([F:21])([O:10][C:11]1[CH:12]=[C:13]([NH:17][C:18]([NH2:20])=[NH:19])[CH:14]=[CH:15][CH:16]=1)[CH:7]([F:9])[F:8].CN(C)[CH:24]=[CH:25][C:26]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)=O.[OH-].[Na+]>CC(O)C>[F:5][C:6]([F:21])([O:10][C:11]1[CH:12]=[C:13]([NH:17][C:18]2[N:20]=[C:26]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)[CH:25]=[CH:24][N:19]=2)[CH:14]=[CH:15][CH:16]=1)[CH:7]([F:8])[F:9]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 605938(2E)-1-(4-chlorophenyl)-3-(dimethylamino)prop-2-en-1-oneHCID 1785125183-(1,1,2,2-Tetrafluoroethoxy)phenylguanidine nitrate

Produkt 1

HCID 19966997[4-(4-Chloro-phenyl)-pyrimidin-2-yl]-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

539 mg (2.15 mmol) of 3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl-guanidine nitrate are added to a solution of 450 mg (2.15 mmol) of 3-dimethylamino-1-(4-chloro-phenyl)-2-propen-1-one in 5.5 ml of 2-propanol. After the addition of 94.5 mg (2.36 mmol) of sodium hydroxide, the reaction mixture is boiled under reflux for 29 h. After cooling to RT, the product is isolated by filtration and washed with 1-propanol and water. After drying at 60° under HV, N-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-4-(4-chloro-phenyl)-2-pyrimidineamine is obtained; Rf =0.45 (methylene chloride:methanol =98:2), MS: 397 (M+), m.p. 133°-135°.

Aufarbeitung

  1. temperatureunder reflux for 29 h
  2. customthe product is isolated by filtration
  3. washwashed with 1-propanol and water
  4. customAfter drying at 60° under HV

Quellen und Nachweise

ORD-Eintrag
ord-32387682b29b476d94088b49d2225dd9
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05612340

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