3,4,5-Trimethoxybenzaldehyde → HCID 24988117, Verbindung

HRID 507260Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 507260
[O:1]=[C:2]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[S:4][CH:3]1[CH2:12][C:13]([NH:15][NH2:16])=[O:14].[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[CH:22]=O.ClCCCl.C(O)C>C(O)C.C(O)(=O)C>[O:1]=[C:2]1[CH:3]([CH2:12][C:13]([NH:15]/[N:16]=[CH:22]/[C:21]2[CH:24]=[C:25]([O:29][CH3:30])[C:26]([O:27][CH3:28])=[C:19]([O:18][CH3:17])[CH:20]=2)=[O:14])[S:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[NH:7]1

Komponenten

6

Edukt 3

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 34500263,4-Dihydro-3-oxo-2H-1,4-benzothiazine-2-acetic acid hydrazideHCID 229016121,2-Dichloroethane ethanol

Produkt 1

HCID 24988117HCID 24988117, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

In a round-bottom glass flask equipped with a magnetic stir bar (3-Oxo-3,4-dihydro-2H-benzo[1,4]thiazin-2-yl)-acetic acid hydrazide (1 eq. 0.063 mmol; 15 mg) was dissolved in ethanol (3 mL) at room temperature. To this well stirred solution, acetic acid (˜3 drops) and 3,4,5-trimethoxy-benzaldehyde solution (0.063 mmol; 12.4 mg dissolved in 0.5 mL of ethanol) were added, and the reaction mixture was stirred for another 5 hours at ambient temperature and monitored by TLC (typically with 1,2-dichloroethane-ethanol 5:1). The mixture was then concentrated under vacuum using a rotary evaporator. The crude product was diluted with hexanes and triturated. The precipitated solid product was transferred to a glass fiber funnel, the supernatant was removed by vacuum filtration and the solid was washed thoroughly with n-hexane twice to yield: 16 mg (61%) of 1-1.

Aufarbeitung

  1. concentrationThe mixture was then concentrated under vacuum
  2. customa rotary evaporator
  3. additionThe crude product was diluted with hexanes
  4. customtriturated
  5. customThe precipitated solid product was transferred to a glass fiber funnel
  6. customthe supernatant was removed by vacuum filtration
  7. washthe solid was washed thoroughly with n-hexane twice to yield: 16 mg (61%) of 1-1

Quellen und Nachweise

ORD-Eintrag
ord-446dd4775bbe4a03a3babdfe1b9ddd69
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786139B2

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