5H-Dibenzo(a,d)cycloheptene, 10,11-dihydro-5-chloro- → 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile

HRID 1456681ノート

反応式

HRID 1456681 の反応式
[Sn](Cl)(Cl)(Cl)Cl.Cl[CH:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][CH2:10][C:9]2[CH:18]=[CH:19][CH:20]=[CH:21][C:8]1=2.C[Si]([C:26]#[N:27])(C)C>C(Cl)Cl.O>[C:26]([CH:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][CH2:10][C:9]2[CH:18]=[CH:19][CH:20]=[CH:21][C:8]1=2)#[N:27]

参加物

6

反応物 3

HCID 145875H-Dibenzo(a,d)cycloheptene, 10,11-dihydro-5-chloro-HCID 24287Tin tetrachlorideHCID 82115Trimethylsilyl cyanide

生成物 1

HCID 1409111110,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile収率 88.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

6.0 g (23.0 mmol) of tin tetrachloride are slowly added to a solution of 21.1 g (92.3 mmol) of 5-chloro-10,11-dihydro-5H-dibenzo[a,d]cycloheptene [V. Mychajlyszyn et al, Coll. Czech. Chem. Comm. 24, 3955 (1959)] and 11.3 g (114 mmol) of trimethylsilylcyanide in 150 ml of methylene chloride. The reaction mixture is stirred at room temperature for 10 hours and then diluted with 150 ml of methylene chloride, and 200 ml of water are added. The organic phase is separated off, washed with dilute sodium bicarbonate solution, dried over sodium sulfate and concentrated on a vacuum rotary evaporator. Crystallization of the residue from toluene gives 18.0 g (88.9%) of 5-cyano-10,11-dihydro-5H-dibenzo[a,d]-cycloheptene, melting point 89°-90° C. (compound (104), Table 1).

後処理

  1. additionare added
  2. customThe organic phase is separated off
  3. washwashed with dilute sodium bicarbonate solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated on a vacuum rotary evaporator
  6. customCrystallization of the residue from toluene

出典と根拠

ORDレコード
ord-c7af6449320b467ca13f1ccdb638a4d1
出典データセット
uspto-grants-1998_12
特許番号
US05844024

反応ノート

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