4-Cyanoacetanilide → HCID 69058617, compound

HRID 2103728Notes

Reaction equation

HRID 2103728 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:12])[CH3:11])=[CH:5][CH:4]=1)#[N:2].[Li]CCCC.[Cl:18][CH2:19][CH2:20][CH2:21][CH2:22]I>C1COCC1.CCCCCC>[Cl:18][CH2:19][CH2:20][CH2:21][CH2:22][N:9]([C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=1)[C:10](=[O:12])[CH3:11]

Participants

6

Reactant 3

HCID 372564-CyanoacetanilideHCID 825271-Chloro-4-iodobutaneHCID 178418339Butyllithium

Product 1

HCID 69058617HCID 69058617, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

9 g (54.1 mmol) of N-(4-cyanophenyl)acetamide are dissolved in 100 ml of THF. The mixture is cooled to 0° C. before the dropwise addition of 51 ml of a 1.6 N solution in hexane of nBuLi (1.5 eq.). The solution is left for one hour to return to ambient temperature and is then cooled to 0° C. before the dropwise addition of 9.9 ml of 1-chloro-4-iodobutane (81 mmol). The reaction mixture is stirred at ambient temperature for 18 h and then hydrolysed with a saturated aqueous solution of ammonium chloride (100 ml) and extracted with ethyl acetate. The organic phases are combined, dried over magnesium sulphate and concentrated. Purification by chromatography on silica (eluant: petroleum ether/ethyl acetate: 1/1) yields a yellow oil containing the expected product.

Workup

  1. customto return to ambient temperature
  2. extractionhydrolysed with a saturated aqueous solution of ammonium chloride (100 ml) and extracted with ethyl acetate
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. customPurification by chromatography on silica (eluant: petroleum ether/ethyl acetate: 1/1)
  6. customyields a yellow oil

Sources & evidence

ORD record
ord-a18af5e5e0c34bc6afafaff429a11712
Source dataset
uspto-grants-2009_08
Patent number
US07576120B2

Reaction notes

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