Acetonitrile → 3-Bromo-4-(cyanomethyl)phenylcyclopropane carboxamide

HRID 39163ノート

反応式

HRID 39163 の反応式
O1C2C=CC(C3(C(N[C:16]4[CH:21]=[CH:20][C:19]([CH2:22]O)=[C:18]([Br:24])[CH:17]=4)=O)CC3)=CC=2OC1.CS(Cl)(=O)=[O:27].C([N:33]([CH2:37][CH3:38])C(C)C)(C)C.[C-:39]#[N:40].[K+].[C:42](#N)[CH3:43]>ClCCl>[Br:24][C:18]1[CH:17]=[C:16]([C:38]2([C:37]([NH2:33])=[O:27])[CH2:43][CH2:42]2)[CH:21]=[CH:20][C:19]=1[CH2:22][C:39]#[N:40]

参加物

7

反応物 5

HCID 6342AcetonitrileHCID 9032Potassium CyanideHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 592062471-(benzo[d][1,3]dioxol-5-yl)-N-(3-bromo-4-(hydroxymethyl)phenyl)cyclopropanecarboxamide

生成物 1

HCID 866458503-Bromo-4-(cyanomethyl)phenylcyclopropane carboxamide収率 46%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

1-(Benzo[d][1,3]dioxol-5-yl)-N-(3-bromo-4-(hydroxymethyl)phenyl)cyclopropane-carboxamide (1.08 g, 2.78 mmol), methanesulfonyl chloride (0.24 mL, 3.1 mmol), and N,N-diisopropylethylamine (0.72 mL, 4.1 mmol) were dissolved in acetonitrile (27 mL) at 25° C. After complete dissolution, KCN (450 mg, 6.95 mmol) was added and the reaction was stirred for 14 d. The reaction was diluted with dichloromethane (25 mL) and washed with water (25 mL). The organic extracts were dried over Na2SO4 and evaporated. The crude product was purified by chromatography on silica gel (eluting with 0-100% ethyl acetate in hexanes) to afford 1-(benzo[d][1,3]dioxol-5-yl)-N-(3-bromo-4-(cyanomethyl)phenylcyclopropane carboxamide (514 mg, 46%). ESI-MS m/z calc. 398.0, found 399.1 (M+1)+; retention time 3.24 minutes.

後処理

  1. additionwas added
  2. washwashed with water (25 mL)
  3. dry with materialThe organic extracts were dried over Na2SO4
  4. customevaporated
  5. customThe crude product was purified by chromatography on silica gel (eluting with 0-100% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-81c683f1e96a4aeca24c939b9be25311
出典データセット
uspto-grants-2013_09
特許番号
US08524767B2

反応ノート

読み込み中…