Benzene, 1-bromo-3-(trifluoromethyl)- → 1-Benzhydryl-2-(m-trifluoromethylbenzimidoyl)azetidine

HRID 1390961ノート

反応式

HRID 1390961 の反応式
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([Mg]Br)[CH:6]=[CH:7][CH:8]=1.BrC1C=C(C(F)(F)F)C=CC=1.[Mg].[CH:25]([N:38]1[CH2:41][CH2:40][CH:39]1[C:42]#[N:43])([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CCOCC>[CH:25]([N:38]1[CH2:41][CH2:40][CH:39]1[C:42](=[NH:43])[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:12])([F:11])[F:1])[CH:4]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

参加物

6

反応物 4

HCID 9817Benzene, 1-bromo-3-(trifluoromethyl)-HCID 5462224MagnesiumHCID 197720721-Benzhydrylazetidine-2-carbonitrileHCID 178506173HCID 178506173、化合物

生成物 1

HCID 203870491-Benzhydryl-2-(m-trifluoromethylbenzimidoyl)azetidine

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒3 回

実験手順

Suspend m-trifluoromethylphenylmagnesium bromide in ether by adding a solution of 18 g of m-bromobenzotrifluoride in 30 ml of ether to a stirred suspension of 1.94 g of magnesium turnings in 20 ml of dry ether. Upon completion of addition, allow the reaction mixture to cool to room temperature and add 7.95 g of 1-benzhydryl-2-cyanoazetidine. Stir the mixture for 18 hours at room temperature, cool to 0° C. or lower, and quench by the dropwise addition of 50 ml of water. Add 15 ml of ether and 25 ml of methylene chloride and filter the mixture through a pad of diatomaceous earth, such as commercially available Celite. Remove the aqueous layer of the filtrate. Wash the organic phase with water and dry over anhydrous sodium sulfate. Remove the solvent in vacuo to obtain the title compound as an oil. By suitable substitution, analogous halo compounds can be prepared.

後処理

  1. additionUpon completion of addition
  2. temperaturecool to 0° C.
  3. customlower, and quench by the dropwise addition of 50 ml of water
  4. additionAdd 15 ml of ether and 25 ml of methylene chloride
  5. filtrationfilter the mixture through a pad of diatomaceous earth
  6. customRemove the aqueous layer of the filtrate
  7. washWash the organic phase with water
  8. dry with materialdry over anhydrous sodium sulfate
  9. customRemove the solvent in vacuo

出典と根拠

ORDレコード
ord-1d47642a5bc94e3ba73c7130b4007e00
出典データセット
uspto-grants-1979_02
特許番号
US04140780

反応ノート

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