Dimethylformamide → 7-(2-{1-[4-Hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethylidene}hydrazinecarbothioamido)-4H-benzo[1,4]oxazin-3-one

HRID 1094939Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1094939
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]2[NH:6][C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.CN(C)C=O.[C:18](N1C=CN=C1)(N1C=CN=C1)=[S:19].[N:30](=[C:32]([C:34]1[C:38]([OH:39])=[C:37]([C:40]2[CH:45]=[CH:44][C:43]([C:46]([F:49])([F:48])[F:47])=[CH:42][CH:41]=2)[N:36]([CH3:50])[N:35]=1)[CH3:33])[NH2:31]>O>[OH:39][C:38]1[C:34]([C:32](=[N:30][NH:31][C:18](=[S:19])[NH:1][C:2]2[CH:12]=[CH:11][C:5]3[NH:6][C:7](=[O:10])[CH2:8][O:9][C:4]=3[CH:3]=2)[CH3:33])=[N:35][N:36]([CH3:50])[C:37]=1[C:40]1[CH:41]=[CH:42][C:43]([C:46]([F:49])([F:48])[F:47])=[CH:44][CH:45]=1

Komponenten

6

Edukt 4

HCID 6228Dimethylformamide2×HCID 802641,1'-ThiocarbonyldiimidazoleHCID 27641827-amino-3,4-dihydro-2H-1,4-benzoxazin-3-oneHCID 72360113HCID 72360113, Verbindung

Produkt 1

HCID 765977637-(2-{1-[4-Hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethylidene}hydrazinecarbothioamido)-4H-benzo[1,4]oxazin-3-oneAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

7-Amino-4H-benzo[1,4]oxazin-3-one (33 mg, 0.203 mmol) was stirred with a dimethylformamide solution of thiocarbonyldiimidazole (0.1 M, 2.03 mL, 0.203 mmol) at room temperature for 1 hour and then with a dimethylformamide solution of 3-(1-hydrazonoethyl)-1-methyl-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-4-ol prepared in Reference Synthetic Example 14 (0.1 M, 1.36 mL, 0.135 mmol) at room temperature for 4 hours Water was added, and the precipitated solid was collected by filtration, washed with water and dried. After addition of chloroform, the solid was collected by filtration washed with chloroform and dried to give 33.6 mg of the desired product (yield 49%).

Aufarbeitung

  1. additionwas added
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with water
  4. customdried
  5. additionAfter addition of chloroform
  6. filtrationthe solid was collected by filtration
  7. washwashed with chloroform
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c77f0600e5e24a03bf3250106be82b89
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08134013B2

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