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Hydrochloric Acid → 2-(2-chloro-2-phenylacetamido)-beta-oxo-N-(2-thiazolyl)-3-trifluoromethyl-benzene-propanamide

HRID 648734
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 648734
C([Li])CCC.[S:6]1[CH:10]=[CH:9][N:8]=[C:7]1[NH:11][C:12](=[O:14])[CH3:13].Cl[C:16]1[CH:37]=[CH:36][CH:35]=[CH:34][C:17]=1[CH2:18][C:19]1[O:20][C:21]2[C:29]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:27]=[CH:26][C:22]=2[C:23](=O)[N:24]=1.[ClH:38].[O:39]1CCCC1>CCCCCC>[Cl:38][CH:18]([C:17]1[CH:16]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:19]([NH:24][C:23]1[C:29]([C:30]([F:31])([F:32])[F:33])=[CH:28][CH:27]=[CH:26][C:22]=1[C:21](=[O:20])[CH2:13][C:12]([NH:11][C:7]1[S:6][CH:10]=[CH:9][N:8]=1)=[O:14])=[O:39]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 176252-AcetamidothiazoleHCID 201456882-chlorobenzyl-8-trifluoromethyl-4H-1,3-benzoxazin-4-oneHCID 178418339Butyllithium

Produkt 1

HCID 134230822-(2-chloro-2-phenylacetamido)-beta-oxo-N-(2-thiazolyl)-3-trifluoromethyl-benzene-propanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

28.6 ml of a solution of 1.4 moles of n-butyllithium per liter of hexane were added at 0° C. to a solution of 2.84 g of N-(2-thiazolyl)-acetamide in 100 ml of tetrahydrofuran and 3.39 g of the product of Step A were added to the mixture cooled to -70° C. The mixture was poured into ice and N hydrochloric acid and was extracted with ether. The organic phase was washed successively with N-hydrochloric acid and with water, dried and evaporated to dryness under reduced pressure. The residue was empasted with 50 ml of ether and was vacuum filtered. The product was washed and dried under reduced pressure at 50° C. to obtain 3.2 g of 2-(2-chloro-2-phenylacetamido)-β-oxo-N-(2-thiazolyl)-3-trifluoromethyl-benzenepropanamide melting at 185° C. (decomposition).

Aufarbeitung

  1. additionwere added to the mixture
  2. extractionwas extracted with ether
  3. washThe organic phase was washed successively with N-hydrochloric acid and with water
  4. customdried
  5. customevaporated to dryness under reduced pressure
  6. filtrationfiltered
  7. washThe product was washed
  8. customdried under reduced pressure at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-ed7a1c5592034e3d86487f9563f133db
Quelldatensatz
uspto-grants-1988_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04736033

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