Cyanamide → [4-Amino-2-[[4-(4-methyl-1-piperazinyl)phenyl]amino]-5-thiazolyl](4-chloro-3-nitrophenyl)methanone

HRID 353736Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 353736
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)=[C:2]=[S:3].[N:17]#[C:18][NH2:19].CC(C)([O-])C.[K+].Br[CH2:27][C:28]([C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([N+:37]([O-:39])=[O:38])[CH:31]=1)=[O:29]>C(#N)C.O>[NH2:17][C:18]1[N:19]=[C:2]([NH:1][C:4]2[CH:5]=[CH:6][C:7]([N:10]3[CH2:11][CH2:12][N:13]([CH3:16])[CH2:14][CH2:15]3)=[CH:8][CH:9]=2)[S:3][C:27]=1[C:28]([C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([N+:37]([O-:39])=[O:38])[CH:31]=1)=[O:29]

Komponenten

7

Edukt 4

HCID 9864CyanamideHCID 27783302-Bromo-1-(4-chloro-3-nitrophenyl)ethan-1-oneHCID 137183971-(4-Isothiocyanatophenyl)-4-methylpiperazineHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 10162409[4-Amino-2-[[4-(4-methyl-1-piperazinyl)phenyl]amino]-5-thiazolyl](4-chloro-3-nitrophenyl)methanoneAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a mixture of 1-(4-isothiocyanatophenyl)-4-methylpiperazine (of Example 1; 1.0 g, 4.3 mmol) and cyanamide (0.2 g, 4.8 mmol) in acetonitrile (43 mL), a solution of potassium tert-butoxide (43 mL, 0.1 M in tert-BuOH) was added. After 30 minutes at room temperature, 2-bromo-1-(4-chloro-3-nitro-phenyl)ethanone (1.2 g, 4.3 mmol) (Maybridge Chemical Company Ltd.) was added. The reaction mixture was stirred for 4h and then poured into 50 mL of water. The product was collected by filtration, washed with water and diethyl ether. The yellow powder was dried in vacuo to provide 0.9 g (45% yield) of [4-amino-2-[[4-(4-methyl-1-piperazinyl)phenyl]amino]-5-thiazolyl](4-chloro-3-nitrophenyl)methanone.

Aufarbeitung

  1. filtrationThe product was collected by filtration
  2. washwashed with water and diethyl ether
  3. customThe yellow powder was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-55ef5019a79e498c98eb43d270a538f6
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06756374B2

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