Dibenzothiazepinone → N-[4-(11H-Dibenzo[b,f][1,4]thiazepine-10-carbonyl)-phenyl]-2-methyl-benzamide

HRID 362394

Reaktionsgleichung

Reaktionsgleichung von HRID 362394
O=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6][C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[NH:3]1.B.CSC.C1C2CNC3C=CC=CC=3SC=2C=CC=1.[CH3:36][C:37]1[CH:54]=[CH:53][CH:52]=[CH:51][C:38]=1[C:39]([NH:41][C:42]1[CH:50]=[CH:49][C:45]([C:46](Cl)=[O:47])=[CH:44][CH:43]=1)=[O:40]>O1CCCC1.ClCCl.CN(C)C1C=CN=CC=1.C(N(CC)CC)C>[CH:9]1[C:8]2[CH2:2][N:3]([C:46]([C:45]3[CH:44]=[CH:43][C:42]([NH:41][C:39](=[O:40])[C:38]4[CH:51]=[CH:52][CH:53]=[CH:54][C:37]=4[CH3:36])=[CH:50][CH:49]=3)=[O:47])[C:4]3[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=3[S:6][C:7]=2[CH:12]=[CH:11][CH:10]=1

Komponenten

9

Edukt 4

HCID 374829DibenzothiazepinoneHCID 107074414-[(2-methylbenzoyl)amino]benzoyl ChlorideHCID 1231048210,11-Dihydrodibenzo(b,f)(1,4)thiazepineHCID 12423031(Dimethyl sulfide)trihydroboron

Produkt 1

HCID 15307988N-[4-(11H-Dibenzo[b,f][1,4]thiazepine-10-carbonyl)-phenyl]-2-methyl-benzamideAusbeute 74,3 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

As described for in Reference Example 12, a mixture of 3.3 g of 10,11-dihydro-11-oxodibenz[b,f][1,4]thiazepine, 25 ml of tetrahydrofuran, 4.0 ml of 10 molar borane-dimethylsulfide (2.67 equivalents) in tetrahydrofuran is stirred at room temperature 18 hours to give, after work-up, 10,11-dihydrodibenz[b,f][1,4]thiazepine as white crystals, m.p. 145°-148° C. The preceding compound (3.5 g) is suspended in 25 ml of dichloromethane and a solution of 1.8 g of 4-[(2-methylbenzoyl)amino]benzoyl chloride in 50 ml of dichloromethane added. To the stirred mixture is added 4 ml of triethylamine and 0.2 g of 4-(dimethylamino) pyridine. The mixture is stirred at room temperature for 20 hours. The mixture is filtered and the filtrate concentrated. The residue is purified by chromatography on silica gel with hexane-chloroform-ethyl acetate (2:1:1) as solvent to give 2.2 g of yellow crystals. A sample (0.80 g) is further purified by thick layer chromatography on silica gel with hexane-chloroform-ethyl acetate (2:1:1) as solvent to give 0.50 g of crystals, 76°-78° C.

Aufarbeitung

  1. customto give
  2. stirringThe mixture is stirred at room temperature for 20 hours
  3. filtrationThe mixture is filtered
  4. concentrationthe filtrate concentrated
  5. customThe residue is purified by chromatography on silica gel with hexane-chloroform-ethyl acetate (2:1:1) as solvent

Quellen und Nachweise

ORD-Eintrag
ord-ab8b34cfad104a4aaf76f38679aa9bf3
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05869483

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