Sodium Cyanide → 155380-13-5

HRID 1636997Notes

Reaction equation

HRID 1636997 reaction equation
[C-:1]#[N:2].[Na+].[Cl:4][CH2:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8](Cl)=[O:9]>C(#N)C.CCOCC.N1C2C(=CC=CC=2)C=CC=1>[Cl:4][CH2:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8](=[O:9])[C:1]#[N:2]

Participants

6

Reactant 2

HCID 8929Sodium CyanideHCID 30163952-(Chloromethyl)benzoyl chloride

Product 1

HCID 9812919155380-13-5Yield 97.5%

Reagents, catalysts & solvents 3

HCID 7047QuinolineCatalystHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of acetonitrile (100 ml), 95% sodium cyanide (6.19 g), 95% cuprous iodide (2.00 g) and quinoline (0.13 g) was stirred at 60° C. A solution of 2-chloromethylbenzoyl chloride (19.0 g) in acetonitrile (100 ml) was added dropwise to the reaction mixture over 3 hours. After completion of the addition, the mixture was stirred at 60° C. for 5 hours. After the reaction mixture was cooled by allowing it to stand, the reaction mixture was diluted with ether, and washed successively with water, a saturated aqueous solution of sodium bicarbonate and water. The ether layer thus obtained was dried over anhydrous sodium sulfate and at the same time decolorized with Norit SX-3. Evaporation of the solvent under reduced pressure gave the crude title compound (17.6 g, purity: about 72% determined by 1H-NMR analysis).

Workup

  1. additionAfter completion of the addition
  2. stirringthe mixture was stirred at 60° C. for 5 hours
  3. temperatureAfter the reaction mixture was cooled
  4. washwashed successively with water
  5. customThe ether layer thus obtained
  6. dry with materialwas dried over anhydrous sodium sulfate and at the same time
  7. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-d2314cc2a35b4d80b854c35c96831f15
Source dataset
uspto-grants-2000_03
Patent number
US06037495

Reaction notes

Loading…