Glycol monoethyl ether → 2-(2,6-Dichlorophenyl)acetamide

HRID 1857957Notes

Reaction equation

HRID 1857957 reaction equation
[Na].[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:4]=1[CH2:10][C:11]#[N:12].C([O:15]CCO)C>C([O-])(O)=O.[Na+]>[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:4]=1[CH2:10][C:11]([NH2:12])=[O:15]

Participants

5

Reactant 3

HCID 8076Glycol monoethyl etherHCID 76678(2,6-Dichlorophenyl)acetonitrileHCID 5360545Sodium

Product 1

HCID 34223792-(2,6-Dichlorophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Alternative Conditions. To a solution of sodium (169 mg, 7.35 mmol) dissolved in 2-ethoxyethanol (7.0 mL) was added 2,6-dichlorophenylacetonitrile (1.40 g, 7.53 mmol) and (IV) (502 mg, 3.66 mmol), and the mixture was then stirred at reflux for 30 minutes. The resulting solution was diluted with aqueous NaHCO3 (50 mL) and extracted with EtOAc (3×50 mL). The solvents were removed under reduced pressure, then chromatography of the residue on silica gel, eluting with 2-3% MeOH/CH2Cl2, gave firstly a mixed fraction, which on crystallisation from CHCl3 /light petroleum gave 2,6-dichlorophenylacetamide (165 mg): mp (MeOH/CH2Cl2) 211.5-213° C.

Workup

  1. temperatureat reflux for 30 minutes
  2. extractionextracted with EtOAc (3×50 mL)
  3. customThe solvents were removed under reduced pressure
  4. washchromatography of the residue on silica gel, eluting with 2-3% MeOH/CH2Cl2
  5. customgave firstly a mixed fraction, which
  6. customon crystallisation from CHCl3 /light petroleum

Sources & evidence

ORD record
ord-1664a966164b437c8bc03304594cc309
Source dataset
uspto-grants-2000_11
Patent number
US06150359

Reaction notes

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