Cyanogen Bromide → 4,5-Dichloro-2-(3,4-dichlorophenyl)pyrrole-1,3-dicarbonitrile

HRID 1033576

反応式

HRID 1033576 の反応式
CC(C)([O-])C.[K+].[C:7]([C:9]1[C:13]([Cl:14])=[C:12]([Cl:15])[NH:11][C:10]=1[C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=1)#[N:8].[N:24]#[C:25]Br>C1COCC1>[Cl:14][C:13]1[C:9]([C:7]#[N:8])=[C:10]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[N:11]([C:25]#[N:24])[C:12]=1[Cl:15]

参加物

5

反応物 3

HCID 10476Cyanogen BromideHCID 1835554,5-dichloro-2-(3,4-dichlorophenyl)-1H-pyrrole-3-carbonitrileHCID 23665647Potassium tert-butoxide

生成物 1

HCID 150101564,5-Dichloro-2-(3,4-dichlorophenyl)pyrrole-1,3-dicarbonitrile収率 64.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Potassium t-butoxide (617 mg, 55 mmol) is added in portions to a solution of 3-cyano-4,5-dichloro 2-(3,4-dichlorophenyl)pyrrole (1.52 g, 5 mmol) in anhydrous THF (20 mL). After 30 minutes, a solution of cyanogen bromide (583 mg, 5.5 mmol) in THF (1 mL) is added. The reaction mixture is stored at room temperature overnight. The solvent is removed in a rotary evaporator. The residue is treated with water and extracted with ethyl acetate. The organic layer is washed with water and saturated sodium chloride and dried (MgSO4). Evaporation and crystallization of the residue from ethyl acetate gives while crystals (1.07 g); mp 250.5°-252.0° C.; IR (nujol) 2255, 2245 cm-1 (CN); 13C NMR (DMSO-d6) 102.7 (N--CN), 113.7 (3-CN); Mass spectrum 331.9 (M+1).

後処理

  1. waitThe reaction mixture is stored at room temperature overnight
  2. customThe solvent is removed in a rotary evaporator
  3. additionThe residue is treated with water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer is washed with water and saturated sodium chloride
  6. dry with materialdried (MgSO4)
  7. customEvaporation and crystallization of the residue from ethyl acetate

出典と根拠

ORDレコード
ord-2a4f6d430cfc4aaf9f0e0611a7698463
出典データセット
uspto-grants-1994_05
特許番号
US05310938

関連ノート

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