Chloroacetyl chloride → 2-Chloro-N-[3,4-bis(phenylmethoxy)phenyl]acetamide

HRID 4112

Reaction equation

HRID 4112 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][C:15]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[NH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:24][CH2:25][C:26](Cl)=[O:27].C(=O)(O)[O-].[K+]>C(#N)C.O>[Cl:24][CH2:25][C:26]([NH:12][C:11]1[CH:13]=[CH:14][C:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=1)=[O:27]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chloride2×HCID 516893Potassium BicarbonateHCID 122537843,4-Dibenzyloxy aniline

Product 1

HCID 201534662-Chloro-N-[3,4-bis(phenylmethoxy)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To 7.7 g (25 mmol) of 3,4-dibenzyloxyaniline in 50 ml of 1:1 acetonitrile/water at 0° C. was added chloroacetyl chloride (3.0 ml) while keeping the pH at 6.5 with saturated aqueous potassium bicarbonate. When the pH remained constant for 15 minutes, an additional 3 ml of chloroacetyl chloride was added in small portions while maintaining the pH at 6.5. When the pH remained constant for 15 minutes, the acetonitrile was evaporated, and the resulting aqueous solution was filtered. The precipitate was washed thoroughly with water to yield, upon drying in vacuo, 8.98 g of the title compound.

Workup

  1. temperaturewhile maintaining the pH at 6.5
  2. waitWhen the pH remained constant for 15 minutes
  3. customthe acetonitrile was evaporated
  4. filtrationthe resulting aqueous solution was filtered
  5. washThe precipitate was washed thoroughly with water
  6. customto yield
  7. dry with materialupon drying in vacuo, 8.98 g of the title compound

Sources & evidence

ORD record
ord-b9d7e217a7e7454187283988eab03121
Source dataset
uspto-grants-1988_02
Patent number
US04723002

Linked notes

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