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

HRID 39163노트

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HRID 39163 반응식
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]

참가 물질

7

반응물 5

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

생성물 1

HCID 866458503-Bromo-4-(cyanomethyl)phenylcyclopropane carboxamide수율 46%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-81c683f1e96a4aeca24c939b9be25311
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524767B2

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