Stannous chloride dihydrate → Dibenzyl 5-aminoisophthalate

HRID 581167Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 581167
[CH2:1]([O:8][C:9]([C:11]1[CH:12]=[C:13]([N+:27]([O-])=O)[CH:14]=[C:15]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH:16]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.[Sn](Cl)Cl.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[CH2:1]([O:8][C:9]([C:11]1[CH:12]=[C:13]([CH:14]=[C:15]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH:16]=1)[NH2:27])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 190639261,3-Dibenzyl 5-nitrobenzene-1,3-dicarboxylate

Produkt 1

HCID 7023592Dibenzyl 5-aminoisophthalateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

3,5-dibenzyloxycarbonyl-nitrobenzene (3.91 g, 10 mol) was dissolved in ethyl acetate (50 ml) and tin(II)chloride dihydrate (11.27 g, 50 mmol) was added and the mixture stirred and heated at 70 under an atmosphere of nitrogen for 1 h. The mixture was poured carefully onto 5% sodium hydrogencarbonate solution (200 ml) and a further aliquot of ethyl acetate (100 ml) was added. After shaking the organic layer was separated and the aqueous layer was extracted with more ethyl acetate (50 ml). The combined organic layers were washed with brine, and dried, filtered and evaporated to leave a pale yellow solid (3.25 g, 90%), 1H NMR (CDCl3) δ 8.1 (1H, d), 7.5 (12H, m), 5.4 (4H, s), 3.8 (2H, bs).

Aufarbeitung

  1. temperatureheated at 70 under an atmosphere of nitrogen for 1 h
  2. stirringAfter shaking the organic layer
  3. customwas separated
  4. extractionthe aqueous layer was extracted with more ethyl acetate (50 ml)
  5. washThe combined organic layers were washed with brine
  6. customdried
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-7ef8a3f3ac624f16b74f69112de1650b
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05919829

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