Water → N-{2-[6-(cyanomethyl)-1,3-benzodioxol-5-yl]ethyl}acetamide

HRID 462098Notes

Reaction equation

HRID 462098 reaction equation
Cl[CH2:2][C:3]1[C:8]([CH2:9][CH2:10][NH:11][C:12](=[O:14])[CH3:13])=[CH:7][C:6]2[O:15][CH2:16][O:17][C:5]=2[CH:4]=1.[C-:18]#[N:19].[Na+].O>CS(C)=O>[C:18]([CH2:2][C:3]1[C:8]([CH2:9][CH2:10][NH:11][C:12](=[O:14])[CH3:13])=[CH:7][C:6]2[O:15][CH2:16][O:17][C:5]=2[CH:4]=1)#[N:19]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 21824570N-(6-Chloromethyl-3,4-methylenedioxyphenethyl) acetamide

Product 1

HCID 1236400N-{2-[6-(cyanomethyl)-1,3-benzodioxol-5-yl]ethyl}acetamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4.7 g of N-(6-chloromethyl-3,4-methylenedioxyphenethyl) acetamide was dissolved in 10 ml of DMSO and 1.32 g (0.028 mole) of sodium cyanide added to the stirred solution. Within a few minutes, the temperature rose from 25° to 32° C. After 1.5 hrs at ambient temperature the mixture was poured into ice and water. The suspension was extracted with three 50-ml portions of benzene. The benzene layers were washed with saturated brine six times, then with water, the solution dried, and the solvent distilled in the rotary evaporator leaving the above-named product as a crystalline solid, m.p. 153.3-155.5.

Workup

  1. waitWithin a few minutes
  2. customrose from 25° to 32° C
  3. extractionThe suspension was extracted with three 50-ml portions of benzene
  4. washThe benzene layers were washed with saturated brine six times
  5. dry with materialwith water, the solution dried
  6. distillationthe solvent distilled in the rotary evaporator

Sources & evidence

ORD record
ord-8a1e2e70c97043dd951e32df7c6106a4
Source dataset
uspto-grants-1977_12
Patent number
US04065473

Reaction notes

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