Hydrochloric Acid → 5-Benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-N-phenylbenzamide

HRID 2075954Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2075954
[CH2:1]([O:8][C:9]1[C:10]([O:24][CH3:25])=[CH:11][C:12]([C:18]2[N:22]=[C:21]([CH3:23])[O:20][N:19]=2)=[C:13]([CH:17]=1)[C:14](O)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2N=N1.NC1C=CC=CC=1.Cl>C(OCC)(=O)C.C(N(CC)CC)C.CN(C)C=O.C(Cl)Cl>[CH2:1]([O:8][C:9]1[C:10]([O:24][CH3:25])=[CH:11][C:12]([C:18]2[N:22]=[C:21]([CH3:23])[O:20][N:19]=2)=[C:13]([CH:17]=1)[C:14]([NH:27][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:30]=1)=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 757711-HydroxybenzotriazoleHCID 670964845-Benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)benzoic acid

Produkt 1

HCID 595656145-Benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-N-phenylbenzamideAusbeute 730,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 5-benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)benzoic acid (reference example 5-1) (500 mg), benzotriazol-1-yloxytripyrrolidinephosphonium hexafluorophosphate (1.15 g), 1-hydroxybenzotriazole (20 mg), methylene chloride (3 mL) and N,N-dimethylformamide (3 mL) were added aniline (0.2 mL) and triethylamine (0.62 mL). After stirring at room temperature for 4 hours, ethyl acetate and 2 mol/L hydrochloric acid were added to the mixture. The separated organic layer was washed with a 2 mol/L aqueous solution of sodium hydroxide, an aqueous solution of sodium bicarbonate and brine successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was triturated with methanol to give the title compound (449 mg).

Aufarbeitung

  1. washThe separated organic layer was washed with a 2 mol/L aqueous solution of sodium hydroxide
  2. dry with materialan aqueous solution of sodium bicarbonate and brine successively, dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was triturated with methanol

Quellen und Nachweise

ORD-Eintrag
ord-786d362821414037ad9a1261e8129a2e
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07923462B2

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