Triethylamine → HCID 178423541, Verbindung

HRID 471371Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 471371
[CH3:1][C:2]1[CH:10]=[C:9]([C:11]2[CH2:15][C:14]([C:26]([F:29])([F:28])[F:27])([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=3)[O:13][N:12]=2)[CH:8]=[CH:7][C:3]=1[CH:4]=[N:5][OH:6].ClN1C(=O)CCC1=O.[NH2:38][CH2:39][C:40]([NH:42][CH2:43][C:44]([F:47])([F:46])[F:45])=[O:41].C(N(CC)CC)C>CN(C=O)C.C1COCC1>[OH:6][N:5]=[C:4]([NH:38][CH2:39][C:40]([NH:42][CH2:43][C:44]([F:47])([F:46])[F:45])=[O:41])[C:3]1[CH:7]=[CH:8][C:9]([C:11]2[CH2:15][C:14]([C:26]([F:29])([F:27])[F:28])([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:24])([F:25])[F:23])[CH:17]=3)[O:13][N:12]=2)=[CH:10][C:2]=1[CH3:1]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 247051432-Amino-N-(2,2,2-trifluoroethyl)acetamideHCID 1371957342-Methyl-4-[5-trifluoromethyl-5-(3-trifluoromethyl-phenyl)-4,5-dihydro-isoxazol-3-yl]-benzaldehyde oxime

Produkt 1

HCID 178423541HCID 178423541, VerbindungAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a solution of 2-Methyl-4-[5-trifluoromethyl-5-(3-trifluoromethyl-phenyl)-4,5-dihydro-isoxazol-3-yl]-benzaldehyde oxime (250 mg) in DMF (8 mL) was added N-chloro succinimide (84 mg) and heated to 75° C. for 1 h. After cooling, the reaction mixture was poured onto water and extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated in vacuo to ¼ of the original volume to obtain the crude hydroxamic acid chloride. This mixture was added to a solution of 2-amino-N-(2,2,2-trifluoro-ethyl)-acetamide (116 mg) and triethylamine (0.30 mL, 0.21 g) in THF (8 mL) and stirred at room temperature over night. After concentration in vacuo, the mixture was purified by chromatography on silica gel to obtain the title compound (146 mg, 43%).

Aufarbeitung

  1. temperatureAfter cooling
  2. additionthe reaction mixture was poured onto water
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto obtain the crude hydroxamic acid chloride
  7. concentrationAfter concentration in vacuo
  8. customthe mixture was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-a6e347dba44d4beabc58fc6a6665a1f4
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633134B2

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