Sodium Cyanide → 3-(5-Bromobenzo[b]thien-2-yl)-2-(4-methoxyphenyl)butyronitrile

HRID 361914

反応式

HRID 361914 の反応式
[C-:1]#[N:2].[Na+].CS(OC[CH:10]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[CH2:11][C:12]1[S:16][C:15]2[CH:17]=[CH:18][C:19]([Br:21])=[CH:20][C:14]=2[CH:13]=1)(=O)=O.[C:30](OCC)(=O)C.C1(C)C=CC=CC=1>CS(C)=O>[Br:21][C:19]1[CH:18]=[CH:17][C:15]2[S:16][C:12]([CH:11]([CH3:30])[CH:10]([C:22]3[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=3)[C:1]#[N:2])=[CH:13][C:14]=2[CH:20]=1

参加物

5

反応物 3

HCID 8929Sodium CyanideHCID 21584019Toluene ethylacetateHCID 218443143-(5-Bromobenzo[b]thien-2-yl)-2-(4-methoxyphenyl)propyl methanesulfonate

生成物 1

HCID 218443933-(5-Bromobenzo[b]thien-2-yl)-2-(4-methoxyphenyl)butyronitrile

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
80 °C

実験手順

1H-NMR (CDCl3) δ: 3.78 (3H, s), 3.9-4.5 (3H, m), 3.70 (3H, s), 4.3 (2H, m), 6.70-7.80 (8H, m) e) 1.2 g of sodium cyanide was dissolved in 30 ml of dimethyl sulfoxide at a temperature of 90° C. To this was gradually added 18.5 g of 3-(5-bromobenzo[b]thien-2-yl)-2-(4-methoxyphenyl)propyl methanesulfonate, followed by stirring at 80° C. for 1 hour. The resulting reaction solution was mixed with an ethyl acetate/toluene mixture, washed with water, and then dried to distill off the solvent. Crystals thus precipitated were washed with ethanol and dried to obtain 5 g of 3-(5-bromobenzo[b]thien-2-yl)-2-(4-methoxyphenyl)butyronitrile. The same compound was also obtained with a yield of 2 g, by concentrating the ethanol solution resulting from the washing of crystals and subjecting the concentrate to silica gel column chromatography using chloroform as an elution solvent.

後処理

  1. customThe resulting reaction solution
  2. washwashed with water
  3. customdried
  4. distillationto distill off the solvent
  5. customCrystals thus precipitated
  6. washwere washed with ethanol
  7. customdried

出典と根拠

ORDレコード
ord-bd1a795f7ef64356a9bd7fe7a039aee8
出典データセット
uspto-grants-1999_02
特許番号
US05866577

関連ノート

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