Benzyl Chloride → [9-Chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]acetonitrile

HRID 1628722ノート

反応式

HRID 1628722 の反応式
S(Cl)(Cl)=O.[Cl:5][C:6]1[C:14]2[N:13]=[C:12]3[N:15]([C:19]4[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=4[Cl:26])[CH2:16][CH2:17][CH2:18][N:11]3[C:10]=2[C:9]([CH2:27]O)=[CH:8][CH:7]=1.[C-:29]#[N:30].[Na+].C(Cl)C1C=CC=CC=1>O1CCCC1.C(=O)([O-])O.[Na+].O.CS(C)=O.N1C=CC=CC=1>[Cl:5][C:6]1[C:14]2[N:13]=[C:12]3[N:15]([C:19]4[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=4[Cl:26])[CH2:16][CH2:17][CH2:18][N:11]3[C:10]=2[C:9]([CH2:27][C:29]#[N:30])=[CH:8][CH:7]=1

参加物

10

反応物 4

HCID 7503Benzyl ChlorideHCID 8929Sodium CyanideHCID 24386Thionyl ChlorideHCID 57785885[9-Chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]methanol

生成物 1

HCID 57785849[9-Chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]acetonitrile収率 96.1%

試薬・触媒・溶媒 5

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 1049Pyridine溶媒HCID 8028Tetrahydrofuran溶媒HCID 516892Sodium Bicarbonate溶媒2 回

実験手順

Thionyl chloride (0.53 mL, 7.22 mmol) was added to a stirred solution of [9-chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]methanol (1.38 g, 3.61 mmol) and pyridine (0.10 mL) in tetrahydrofuran (30 mL) at 0° C., and the mixture was stirred at room temperature for 90 min. The mixture was diluted with saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. A solution of sodium cyanide (354 mg, 7.22 mmol) in water (1.5 mL) was added to the resulting benzyl chloride in dimethylsulfoxide (12 mL), and the mixture was stirred at room temperature for 14 hr. The mixture was diluted with saturated aqueous sodium hydrogen carbonate, and the precipitate was collected by filtration, washed with diisopropyl ether to give the title compound as a colorless powder (1.36 g, 3.47 mmol, 96% in 2 steps).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. stirringthe mixture was stirred at room temperature for 14 hr
  7. filtrationthe precipitate was collected by filtration
  8. washwashed with diisopropyl ether

出典と根拠

ORDレコード
ord-6291f309e40141b9a5fe17686649644a
出典データセット
uspto-grants-2014_07
特許番号
US08785460B2

反応ノート

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