4-Chloro-2-fluorobenzoyl chloride → HCID 21905770, Verbindung

HRID 1246791

Reaktionsgleichung

Reaktionsgleichung von HRID 1246791
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[C:3]=1[NH2:16].[Cl:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[C:20]([F:27])[CH:19]=1>N1C=CC=CC=1.C(O)C>[Cl:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([NH:16][C:3]2[C:2]([Cl:1])=[N:7][CH:6]=[N:5][C:4]=2[NH:8][C:9]2[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=2)=[O:23])=[C:20]([F:27])[CH:19]=1

Komponenten

5

Edukt 2

HCID 27736014-Chloro-2-fluorobenzoyl chlorideHCID 167263116-Chloro-N~4~-(4-chlorophenyl)pyrimidine-4,5-diamine

Produkt 1

HCID 21905770HCID 21905770, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 1049PyridineLösungsmittel

Versuchsvorschrift

6-Chloro-N4-(4-chlorophenyl)-pyrimidine-4,5-diamine I-(1A-1)a (6.6 g, 26 mmol) in pyridine (30 ml) was cooled to 0° C. and to it was added 4-chloro-2-fluorobenzoyl chloride (5 g, 26 mmol). The reaction was then allowed to warm to ambient temperature overnight. The heterogeneous reaction was diluted with ethanol (50 ml) and the resulting solid collected by filtration. The solids were slurried in toluene, which was then removed under reduced pressure to remove residual ethanol. The solid was slurried in diethyl ether and then collected by filtration to give I-(7A-91)a (8.3 g, 78%): +ACPI MS (M+1) 409.0; 1H NMR (400 MHz, CD3OD) δ 10.60 (s, 1H), 10.10 (s, 1H), 9.19 (s, 1H), 8.74 (t, J=8.1 Hz, 1H), 8.46–8.40 (m, 3H), 8.28 (dd, J=8.7, 2.1 Hz, 1H), 8.20 (d, J=8.7 Hz, 2H).

Aufarbeitung

  1. customThe heterogeneous reaction
  2. filtrationthe resulting solid collected by filtration
  3. customwhich was then removed under reduced pressure
  4. customto remove residual ethanol
  5. filtrationcollected by filtration
  6. customto give I-(7A-91)a (8.3 g, 78%)

Quellen und Nachweise

ORD-Eintrag
ord-1800146ac7c349e69101ea3ed85714e4
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129239B2

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