Chloroacetamide → 2-(3-Aminophenoxy)acetamide

HRID 596600Notes

Reaction equation

HRID 596600 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7].Cl[CH2:12][C:13]([NH2:15])=[O:14]>O>[NH2:7][C:6]1[CH:5]=[C:4]([CH:10]=[CH:9][CH:8]=1)[O:3][CH2:12][C:13]([NH2:15])=[O:14]

Participants

5

Reactant 3

HCID 6580ChloroacetamideHCID 115683-AminophenolHCID 24758Sodium hydride2×

Product 1

HCID 104872522-(3-Aminophenoxy)acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 50% sodium hydride (5.76 g., 0.12 M), 3-hydroxyaniline (13.09 g., 0.12 M) and chloroacetamide (11.22 g., 0.12 M) is stirred at room temperature for 18 hours. The mixture is diluted with water to decompose residual sodium hydride and is then extracted with chloroform. The chloroform extract is dried (MgSO4) and concentrated to an oil under reduced pressure. The addition of chloroform causes it to crystallize. Yield = 10.0g. (50%); m.p. 107°-111° C.

Workup

  1. extractionis then extracted with chloroform
  2. extractionThe chloroform extract
  3. dry with materialis dried (MgSO4)
  4. concentrationconcentrated to an oil under reduced pressure
  5. additionThe addition of chloroform
  6. customto crystallize

Sources & evidence

ORD record
ord-2da4fd088a824536b4dbb61669342ccb
Source dataset
uspto-grants-1977_03
Patent number
US04011324

Reaction notes

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