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

HRID 39163Notes

Reaction equation

HRID 39163 reaction equation
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]

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-81c683f1e96a4aeca24c939b9be25311
Source dataset
uspto-grants-2013_09
Patent number
US08524767B2

Reaction notes

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