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Hydrochloric Acid → 2-(4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)-N,N-dimethylacetamide

HRID 17605
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 17605
C[Al](C)C.CCCCCC.Cl.[CH3:12][NH:13][CH3:14].[C:15]([C:17]1[C:22]2[N:23]=[C:24]([CH:26]3[CH2:28][CH2:27]3)[O:25][C:21]=2[C:20]([CH2:29][C:30]([O:32]C)=O)=[C:19]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:18]=1[CH3:40])#[N:16].Cl>C1(C)C=CC=CC=1>[C:15]([C:17]1[C:22]2[N:23]=[C:24]([CH:26]3[CH2:27][CH2:28]3)[O:25][C:21]=2[C:20]([CH2:29][C:30]([N:13]([CH3:14])[CH3:12])=[O:32])=[C:19]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:18]=1[CH3:40])#[N:16]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 10473Dimethylamine, hydrochlorideHCID 86584505Trimethylaluminum hexaneHCID 86630881Methyl (4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)acetate

Produkt 1

HCID 685875632-(4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)-N,N-dimethylacetamideAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

At room temperature, trimethylaluminium/n-hexane solution (1.03 mol/l) (547 μl, 0.563 mmol) was added to a toluene (2 ml) suspension of dimethylamine hydrochloride (38.3 mg, 0.469 mmol), followed by stirring at room temperature for 30 minutes. Methyl (4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)acetate (I-295) (65.0 mg, 0.188 mmol) was added to the reaction liquid, followed by heating under reflux in an oil bath at 120° C. for 15 hours. With cooling with ice, 1 N hydrochloric acid was added to the reaction liquid. After extraction with ethyl acetate, the obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, then the insoluble matter was separated by filtration, and the residue obtained by concentration was purified by preparative TLC (eluent, chloroform:methanol=10:1, v/v) to obtain the entitled compound (56.0 mg, 83%) as a white solid.

Aufarbeitung

  1. temperatureby heating
  2. temperatureunder reflux in an oil bath at 120° C. for 15 hours
  3. additionwas added to the reaction liquid
  4. extractionAfter extraction with ethyl acetate
  5. washthe obtained organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe insoluble matter was separated by filtration
  8. customthe residue obtained by concentration
  9. customwas purified by preparative TLC (eluent, chloroform

Quellen und Nachweise

ORD-Eintrag
ord-c2b027ba9ea2410a96e4cf33a7a633b3
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07737166B2

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