Triethylamine → N-[4-[(6,11-Dihydro-5H-dibenz[b,e]azepin-5-yl)-carbonyl]phenyl]2-(2-methylpropoxy)benzamide

HRID 1598138ノート

反応式

HRID 1598138 の反応式
Cl[C:2]1[CH:10]=[CH:9][C:8]([N+]([O-])=O)=[CH:7][C:3]=1[C:4](O)=[O:5].C(N(CC)CC)C.[CH2:21]([O:25]C(Cl)=O)[CH:22]([CH3:24])[CH3:23].[NH2:29][C:30]1[CH:52]=[CH:51][C:33]([C:34]([N:36]2[CH2:42][CH2:41][C:40]3[CH:43]=[CH:44][CH:45]=[CH:46][C:39]=3[C:38]3[CH:47]=[CH:48][CH:49]=[CH:50][C:37]2=3)=[O:35])=[CH:32][CH:31]=1>C(Cl)Cl.C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH:47]1[C:38]2[CH2:39][C:40]3[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=3[CH2:42][N:36]([C:34]([C:33]3[CH:51]=[CH:52][C:30]([NH:29][C:4](=[O:5])[C:3]4[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=4[O:25][CH2:21][CH:22]([CH3:23])[CH3:24])=[CH:31][CH:32]=3)=[O:35])[C:37]=2[CH:50]=[CH:49][CH:48]=1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 172872-Chloro-5-nitrobenzoic acidHCID 62365Isobutyl chloroformateHCID 538444955-(4-Aminobenzoyl)-6,7-dihydro-5H-dibenz[b,d]azepine

生成物 1

HCID 67624252N-[4-[(6,11-Dihydro-5H-dibenz[b,e]azepin-5-yl)-carbonyl]phenyl]2-(2-methylpropoxy)benzamide収率 57.9%

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of 0.62 g of 2-chloro-5-nitrobenzoic acid and 0.61 g of triethylamine in 5 ml of methylene chloride is added 0.42 g of isobutylchloroformate at 0° C. The mixture is warmed to room temperature for 30 minutes. A solution of 0.31 g of 5-(4-aminobenzoyl)-6,7-dihydro-5H-dibenz[b,d]azepine in 1 ml of methylene chloride is added followed by 10 mg of N,N-dimethylaminopyridine and 1.0 ml of toluene is added. The mixture is heated at 100° C. for 48 hours. The room temperature reaction mixture is diluted with 15 ml of ethyl acetate and washed with 1N HCl, 1N NaOH, brine and dried (Na2 SO4) and evaporated in vacuo to a residue. The residue is purified by column chromatography on silica gel by elution with 1:2 ethyl acetate-hexane to give 0.28 g of the desired product as a yellow solid. MS(CI):536(M+H).

後処理

  1. additionis added
  2. temperatureThe mixture is heated at 100° C. for 48 hours
  3. customThe room temperature reaction mixture
  4. washwashed with 1N HCl, 1N NaOH, brine
  5. customdried (Na2 SO4)
  6. customevaporated in vacuo to a residue
  7. customThe residue is purified by column chromatography on silica gel by elution with 1:2 ethyl acetate-hexane

出典と根拠

ORDレコード
ord-9c3e3e1b77834ea68b4a35f85c57abda
出典データセット
uspto-grants-1998_04
特許番号
US05736538

反応ノート

読み込み中…