Iodine chloride → 5-(4-Chloro-3-methyl-phenyl)-3-iodo-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine

HRID 558563Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 558563
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:11]3[N:18]=[CH:19][CH:20]=[C:10]3[N:9]=2)=[CH:4][C:3]=1[CH3:21].C([O-])(=O)C.[Na+].[I:27]Cl>C(O)(=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([F:15])([F:16])[F:17])[N:11]3[N:18]=[CH:19][C:20]([I:27])=[C:10]3[N:9]=2)=[CH:4][C:3]=1[CH3:21]

Komponenten

6

Edukt 3

HCID 24640Iodine chlorideHCID 517045Sodium AcetateHCID 670002385-(4-Chloro-3-methyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine

Produkt 1

HCID 670008925-(4-Chloro-3-methyl-phenyl)-3-iodo-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidineAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred solution of 5-(4-chloro-3-methyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine (4.57 g, 15.2 mmol) in acetic acid (25 mL) was added at room temperature sodium acetate (1.36 g, 16.6 mmol) and drop wise a solution of iodine monochloride (2.69 g, 16.6 mmol) in acetic acid (10 mL). The reaction mixture was stirred at room temperature for 19 h, diluted slowly with water (up to 100 mL), stirred at room temperature for 30 min, the precipitate was filtered off, washed with water and dried to give 5-(4-chloro-3-methyl-phenyl)-3-iodo-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine (5.96 g, 93%) as a yellow solid. MS (EI) 436.9 [(M)+]; mp 151° C.

Aufarbeitung

  1. stirringstirred at room temperature for 30 min
  2. filtrationthe precipitate was filtered off
  3. washwashed with water
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-39c15e1653d84ba592637013dce33d84
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063048B2

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