Benzenepropanoyl chloride → 3-phenyl-N-(2-phenyl-1,3-benzoxazol-5-yl)propanamide

HRID 1896746

Reaktionsgleichung

Reaktionsgleichung von HRID 1896746
[C:1]1([C:7]2[O:8][C:9]3[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][C:10]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]1([CH2:23][CH2:24][C:25](Cl)=[O:26])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(C(C)C)CC)(C)C>ClCCl>[C:17]1([CH2:23][CH2:24][C:25]([NH:16][C:13]2[CH:14]=[CH:15][C:9]3[O:8][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[N:11][C:10]=3[CH:12]=2)=[O:26])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 64801Benzenepropanoyl chlorideHCID 81531DiisopropylethylamineHCID 7210592-Phenyl-1,3-benzoxazol-5-amine

Produkt 1

HCID 9760393-phenyl-N-(2-phenyl-1,3-benzoxazol-5-yl)propanamideAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 2-phenylbenzo[d]oxazol-5-amine (50 mg, 0.24 mmol) in dichloromethane (2 mL) at room temperature was added 3-phenylpropanoyl chloride (44.1 mg, 0.26 mmol) followed immediately by diisopropylethylamine (82 μL, 0.48 mmol). The resulting mixture was stirred at room temperature for 16 h. Dichloromethane was added and the organic layer was washed with saturated aqueous Na2CO3. The combined organic layers were dried over anhydrous MgSO4 and evaporated. The resulting solid was dissolved in methanol, passed through an acidic scavenger column (silica-based quaternary amine SPE-AX from Biotage®) and then evaporated to afford 61.1 mg (75%) of the title compound (LCMS RT=6.45 min, MH+ 343.2)

Aufarbeitung

  1. washthe organic layer was washed with saturated aqueous Na2CO3
  2. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  3. customevaporated
  4. dissolutionThe resulting solid was dissolved in methanol
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-03838efeabaa4d9fb9e6abfc63b631db
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518980B2

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