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Potassium Carbonate → 3,5-dimethyl-benzoic acid N'-(2-allyloxymethyl-3-methyl-3-methoxy-benzoyl)-N-tert-butyl-hydrazide

HRID 1774024
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1774024
[C:1]([NH:5][NH:6][C:7](=[O:21])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[C:9]=1[CH2:16][O:17][CH2:18][CH:19]=[CH2:20])([CH3:4])([CH3:3])[CH3:2].[CH3:22][C:23]1[CH:24]=[C:25]([CH:29]=[C:30]([CH3:32])[CH:31]=1)[C:26](Cl)=[O:27].[C:33]([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.O>[CH2:18]([O:17][CH2:16][CH:9]1[C:10]([CH3:33])([O:14][CH3:15])[CH:11]=[CH:12][CH:13]=[C:8]1[C:7]([NH:6][N:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:26](=[O:27])[C:25]1[CH:24]=[C:23]([CH3:22])[CH:31]=[C:30]([CH3:32])[CH:29]=1)=[O:21])[CH:19]=[CH2:20]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 810883,5-Dimethylbenzoyl ChlorideHCID 598385982-allyloxymethyl-3-methoxy-benzoic acid N'-tert-butyl-hydrazide

Produkt 1

HCID 866766673,5-dimethyl-benzoic acid N'-(2-allyloxymethyl-3-methyl-3-methoxy-benzoyl)-N-tert-butyl-hydrazideAusbeute 80,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a flask containing 2.0 g (0.0068 mol) of 2-allyloxymethyl-3-methoxy-benzoic acid N′-tert-butyl-hydrazide dissolved in 15 mL of CH2Cl2 was added 1.27 g (0.0075 mol) of 3,5-dimethylbenzoyl chloride in 10 mL of CH2Cl2 and 2.84 g of K2CO3 (0.02 mol) in 30 mL of H2O. The mixture was stirred at room temperature for 24 hours. The reaction mixture was diluted and partitioned, and the organic phase was dried and solvent was removed in vacuo. The product was purified by silica gel chromatography; eluting in 25% ethyl acetate:hexane fractions, to yield 2.40 g of pure 3,5-dimethyl-benzoic acid N′-(2-allyloxymethyl-3-methyl-3-methoxy-benzoyl)-N-tert-butyl-hydrazide. 1H NMR (CDCl3, 300 MHz) δ (ppm): 7.2 (t, 1H,) 7.1 (s, 1H), 7.05 (d, 2H), 6.95 (m, 2H), 5.9 (m, 1H), 5.2-5.3 (q, 2H), 4.5 (d, 2H), 3.9 (m, 2H), 3.80 (s, 3H), 2.245 (s, 6H), 1.54 7 (s, 9H).

Aufarbeitung

  1. additionThe reaction mixture was diluted
  2. custompartitioned
  3. customthe organic phase was dried
  4. customsolvent was removed in vacuo
  5. customThe product was purified by silica gel chromatography
  6. washeluting in 25% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c9b7fe01e94d48c1a975fe4e06bf6a93
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09255273B2

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