Water → 2-(Phenylamino)acetamide

HRID 556468Notes

Reaction equation

HRID 556468 reaction equation
Cl[CH2:2][C:3]([NH2:5])=[O:4].[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C([O-])([O-])=O.[K+].[K+].O>C(#N)C>[C:7]1([NH:6][CH2:2][C:3]([NH2:5])=[O:4])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6115AnilineHCID 6580ChloroacetamideHCID 11430Potassium Carbonate

Product 1

HCID 153703192-(Phenylamino)acetamideYield 9.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The mixture of 2-chloroacetamide (3.1 g), aniline (3.1 g), K2CO3 (4.5 g) and KI (1 g) in acetonitrile (50 mL) and water (10 mL) was stirred at room temperature for overnight. The solvent was evaporated to about 20 ml under vacuum and the residue was poured into water (40 mL). The solution was extracted with ethyl acetate (3×20 mL), dried over Na2SO4 and concentrated. The residue was purified with chromatography to give 0.48 g of 2-phenylamino-acetamide.

Workup

  1. customThe solvent was evaporated to about 20 ml under vacuum
  2. additionthe residue was poured into water (40 mL)
  3. extractionThe solution was extracted with ethyl acetate (3×20 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified with chromatography

Sources & evidence

ORD record
ord-545928035bf14d599a7b7c55f9f49525
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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