Water → [1,1'-Biphenyl]-4-yl-(5,11-dihydro-10H-dibenzo[b,e][1,4]diazepin-10-yl)methanone

HRID 1070425노트

반응식

HRID 1070425 반응식
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]([C:7](Cl)=[O:8])=[CH:3][CH:2]=1.[CH:16]1[C:26]2[CH2:25][NH:24][C:23]3[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=3[NH:21][C:20]=2[CH:19]=[CH:18][CH:17]=1.O.ClCCl>CN(C)C=O>[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]([C:7]([N:24]2[CH2:25][C:26]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[NH:21][C:22]3[CH:30]=[CH:29][CH:28]=[CH:27][C:23]2=3)=[O:8])=[CH:3][CH:2]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6344DichloromethaneHCID 3604610,11-Dihydro-5h-dibenzo[b,e][1,4]diazepineHCID 841514-Phenylbenzoyl chloride

생성물 1

HCID 9821040[1,1'-Biphenyl]-4-yl-(5,11-dihydro-10H-dibenzo[b,e][1,4]diazepin-10-yl)methanone수율 38.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

4-Biphenyl-carbonyl chloride (1.19 g) dissolved in N,N-dimethylformamide (10 mL) was added dropwise to an ice cooled solution of 5,11-dihydro-10H-dibenzo[b,e][1,4]diazepine (0.98 g) in N,N-dimethylformamide (10 mL). After stirring at room temperature overnight, the reaction mixture was poured into water and dichloromethane. The organic layer was sequentially washed with water and saturated sodium bicarbonate, and dried over anhydrous sodium sulfate. The solution was filtered through a short column of Magnesol® and eluted with additional dichloromethane. The combined eluate was refluxed with gradual addition of hexane until incipient crystallization occurred. Cooling and filtration provided the title compound (0.72 g), m.p. 180-182° C.

후처리

  1. washThe organic layer was sequentially washed with water and saturated sodium bicarbonate
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationThe solution was filtered through a short column of Magnesol®
  4. washeluted with additional dichloromethane
  5. temperatureThe combined eluate was refluxed with gradual addition of hexane until incipient crystallization
  6. temperatureCooling
  7. filtrationfiltration

출처 및 근거

ORD 기록
ord-e38868efe6cf4a08b576ea1e4028954e
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06903091B2

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