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

HRID 39163Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 39163
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]

Komponenten

7

Edukt 5

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-81c683f1e96a4aeca24c939b9be25311
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524767B2

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