2-Methyl-2-butene → 6-chloro-2-[2-cyano-2-({[4-(trifluoromethoxy)phenyl]carbonyl}amino)-propyl]-2H-benzotriazole-4-carboxylic acid

HRID 415752Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 415752
[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[O:31])[C:5]2[C:6]([CH:29]=1)=[N:7][N:8]([CH2:10][C:11]([NH:15][C:16](=[O:28])[C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1)([C:13]#[N:14])[CH3:12])[N:9]=2.CC(=CC)C.Cl[O-].[Na+].P([O-])(O)(O)=[O:41].[Na+]>C1COCC1.O.C(O)(C)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:30]([OH:41])=[O:31])[C:5]2[C:6]([CH:29]=1)=[N:7][N:8]([CH2:10][C:11]([C:13]#[N:14])([NH:15][C:16]([C:17]1[CH:18]=[CH:19][C:20]([O:23][C:24]([F:26])([F:25])[F:27])=[CH:21][CH:22]=1)=[O:28])[CH3:12])[N:9]=2

Komponenten

8

Edukt 4

HCID 105532-Methyl-2-buteneHCID 23665760Sodium HypochloriteHCID 23672064Monosodium phosphateHCID 59327634N-[2-(6-Chloro-4-formyl-2H-benzotriazol-2-yl)-1-cyano-1-methylethyl]-4-trifluoromethoxybenzamide

Produkt 1

HCID 666203556-chloro-2-[2-cyano-2-({[4-(trifluoromethoxy)phenyl]carbonyl}amino)-propyl]-2H-benzotriazole-4-carboxylic acidAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6386tert-ButanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of N-[2-(6-Chloro-4-formyl-2H-benzotriazol-2-yl)-1-cyano-1-methylethyl]-4-trifluoromethoxybenzamide (1.5 g) in a mixture of THF (25 mL), t-butanol (10 mL) and 2-methyl-2-butene was added dropwise the solution of sodium hypochlorite (0.9 g) and sodium dihydrogen phosphate (1.15 g) in water (20 mL). After 4 hour at room temperature, the mixture was concentrated under reduced pressure, diluted with water (50 mL) and acidified to pH 2 with normal HCl. The white solid was filtered and washed with water and dried under vacuum to give the title compound (1.35 g, 87%). MS (ES): M/Z [M+H]=468. 1H NMR: (400 MHz, DMSO-d6): 1.72 (s, 3H), 5.48-5.64 (m, 2H), 7.43 (d, J=8.2 Hz, 2H), 7.83 (d, J=2.0 Hz, 1H), 7.99 (d, J=8.8 Hz, 2H), 8.23 (d, J=1.8 Hz, 0H) and 9.41 (br. s, 1H). 19F NMR (376 MHz, DMSO-d6): −57.1 (s, 3F).

Aufarbeitung

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additiondiluted with water (50 mL)
  3. filtrationThe white solid was filtered
  4. washwashed with water
  5. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-d58b41417665461bb491b514325938ca
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088801B2

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