Triethylamine → 4-(4-Nitrobenzyl)-5,6,7,8-tetrahydro-4H-thieno[3,2-b]-azepine

HRID 862990Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 862990
[S:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][NH:5][C:4]=2[CH:3]=[CH:2]1.C(N(CC)CC)C.[N+:18]([C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=O)=[CH:23][CH:22]=1)([O-:20])=[O:19]>ClCCl>[N+:18]([C:21]1[CH:29]=[CH:28][C:24]([CH2:25][N:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]3[S:1][CH:2]=[CH:3][C:4]2=3)=[CH:23][CH:22]=1)([O-:20])=[O:19]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 118049715,6,7,8-Tetrahydro-4H-thieno[3,2-B]azepine

Produkt 1

HCID 196990844-(4-Nitrobenzyl)-5,6,7,8-tetrahydro-4H-thieno[3,2-b]-azepine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 10.71 g of 5,6,7,8-tetra-hydro-4H-thieno[3,2-b]azepine and 19.4 ml of triethylamine in 150 ml of dichloromethane under argon is added in small portions 4-nitrobenzoyl chloride (exothermic). The mixture is stirred for 3 hours at 25° C. and then washed with water, sodium bicarbonate solution, brine and dried (Na2SO4). The solvent is removed, the residue dried under vacuum and recrystallized by dissolving in hot ethyl acetate and diluting with hexane. Chilling overnight and filtering gives 16 g of light brown crystals, m.p. 141°-142° C.

Aufarbeitung

  1. washwashed with water, sodium bicarbonate solution, brine
  2. dry with materialdried (Na2SO4)
  3. customThe solvent is removed
  4. customthe residue dried under vacuum
  5. customrecrystallized
  6. dissolutionby dissolving in hot ethyl acetate
  7. additiondiluting with hexane
  8. temperatureChilling overnight
  9. filtrationfiltering

Quellen und Nachweise

ORD-Eintrag
ord-4d47a736f47e408194dbdd30ab0b92b2
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05719278

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