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

HRID 1070425ノート

反応式

HRID 1070425 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e38868efe6cf4a08b576ea1e4028954e
出典データセット
uspto-grants-2005_06
特許番号
US06903091B2

反応ノート

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