Hydrochloric Acid → HCID 14174697, compound

HRID 1814735Notes

Reaction equation

HRID 1814735 reaction equation
[N:1]#[C:2][NH2:3].[C:4]1([CH2:10][C:11](Cl)=[O:12])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl>[OH-].[Na+].CC(C)=O>[C:2]([NH:3][C:11](=[O:12])[CH2:10][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)#[N:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7679Phenylacetyl chlorideHCID 9864Cyanamide

Product 1

HCID 14174697HCID 14174697, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 14798Sodium HydroxideSolvent

Procedure

Cyanamide (5.04 g, 120 mmol) was dissolved in 40 mL of 40% sodium hydroxide. To this solution at 0° C., phenylacetyl chloride (3.97 mL, 30 mmol) in 30 mL of acetone was added over 1 h. After stirring at room temperature for 2 h, the reaction mixture as acidified with concentrated HCl to pH 2. Acetone was removed in vacuo. The resulting suspension was extracted with methylene chloride (30 mL×4). The combined organic extracts were washed with brine and dried over magnesium sulfate. Solvent was removed in vacuo to give N-cyano-2-phenylacetamide (3.96 g, 82%) as a yellow oil.

Workup

  1. customAcetone was removed in vacuo
  2. extractionThe resulting suspension was extracted with methylene chloride (30 mL×4)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-551b9571dc334e93a3ce2a8e4091bb03
Source dataset
uspto-grants-2005_04
Patent number
US06878706B1

Reaction notes

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