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

HRID 355939노트

반응식

HRID 355939 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 1140Toluene용매HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ac5758b40b19496db8121ebaff5f46e4
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834461

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