Triethylamine → 10,11-Dihydro-10-(4-nitrobenzoyl)dibenz[b,f][1,4]thiazepine

HRID 362354Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 362354
[CH:1]1[C:6]2[CH2:7][NH:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[S:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[N+:23]([C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1)([O-:25])=[O:24]>ClCCl.CN(C1C=CN=CC=1)C>[N+:23]([C:26]1[CH:27]=[CH:28][C:29]([C:30]([N:8]2[CH2:7][C:6]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[S:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]2=3)=[O:31])=[CH:33][CH:34]=1)([O-:25])=[O:24]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 1231048210,11-Dihydrodibenzo(b,f)(1,4)thiazepine

Produkt 1

HCID 5457007210,11-Dihydro-10-(4-nitrobenzoyl)dibenz[b,f][1,4]thiazepineAusbeute 112,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1.6 g of 10,11-dihydrodibenz[b,f][1,4]thiazepine in 30 ml of dichloromethane is added 0.1 g of 4-(N,N-dimethylamino)pyridine, 4 ml of triethylamine and 1.0 g of 4-nitrobenzoyl chloride and the mixture is stirred for 16 hours. The mixture is poured into ice-water and extracted with 3×150 ml of dichloromethane. The combined organic extract is washed with water, 2N HCl, 2N Na2CO3, water and dried (MgSO4). The solvent is removed in vacuo and the product (2.6 g) purified by chromatography on silica is gel with hexane-ethyl acetate (4:1) as eluent to give 2.2 g of crystals, m.p. 147°-149° C.

Aufarbeitung

  1. extractionextracted with 3×150 ml of dichloromethane
  2. extractionThe combined organic extract
  3. washis washed with water, 2N HCl, 2N Na2CO3, water
  4. dry with materialdried (MgSO4)
  5. customThe solvent is removed in vacuo
  6. customthe product (2.6 g) purified by chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-be832396dc934b20a7511ec1baf80991
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05869483

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