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

HRID 355897

반응식

HRID 355897 반응식
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

참가 물질

9

반응물 4

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

생성물 1

HCID 15307988N-[4-(11H-Dibenzo[b,f][1,4]thiazepine-10-carbonyl)-phenyl]-2-methyl-benzamide수율 16.9%

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회HCID 8028Tetrahydrofuran용매2회HCID 8471Triethylamine용매

실험 절차

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 equiyalents) 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 di-chloromethane 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 solyent to give 2.2 g of yel]ow 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.

후처리

  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 solyent
  6. customto give 2.2 g of yel]ow crystals
  7. customA sample (0.80 g) is further purified by thick layer chromatography on silica gel with hexane-chloroform-ethyl acetate (2:1:1) as solvent

출처 및 근거

ORD 기록
ord-d939e207521c4d19bd111c843bed728f
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834461

연결된 노트

불러오는 중…