Triethylamine → Dibenzothiazepinone

HRID 625175

반응식

HRID 625175 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11](O)=[O:12].CCN=C=NCCCN(C)C.C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1>ClCCl>[CH:14]1[C:10]2[C:11](=[O:12])[NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[S:8][C:9]=2[CH:17]=[CH:16][CH:15]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 109558282-((2-Aminophenyl)thio)benzoic acid

생성물 1

HCID 374829Dibenzothiazepinone

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-((2-aminophenyl)thio)benzoic acid, prepared as described in the previous step, (30 g, 0.122 mol) in dichloromethane (300 mL) was added EDCI (35.2 g, 0.183 mol), triethylamine (51 mL, 0.366 mol) and HOBT (24.7 g, 0.183 mol). The reaction mixture was stirred at room temperature for 12 hours, washed with 1M aq.HCl, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, and dried over MgSO4. The solution was filtered, concentrated, and purified by column chromatography to provide the title compound. ESI-MS (M+1): 228 calc. for C13H9NOS 227. 1H NMR: (CDCl3, 400 MHz): δ (ppm) 7.70-7.67 (m, 1H), 7.58-7.52 (m, 2H), 7.50-7.42 (m, 2H), 7.39-7.35 (m, 1H), 7.24-7.22 (m, 1H), 7.17-7.13 (m, 1H).

후처리

  1. washwashed with 1M aq
  2. dry with materialHCl, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, and dried over MgSO4
  3. filtrationThe solution was filtered
  4. concentrationconcentrated
  5. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-c8b477fb6385461789e5e7bab31d73ee
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09304126B2

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