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

HRID 355897

反応式

HRID 355897 の反応式
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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回HCID 8028Tetrahydrofuran溶媒2 回HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d939e207521c4d19bd111c843bed728f
出典データセット
uspto-grants-1998_11
特許番号
US05834461

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