Chloroacetyl chloride → N-[2-(cyclopent-2-enyl)phenyl]-2-chloroacetamide

HRID 2107512Notes

Reaction equation

HRID 2107512 reaction equation
[CH:1]1([C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[NH2:8])[CH2:5][CH2:4][CH:3]=[CH:2]1.C(=O)(O)[O-].[Na+].[Cl:18][CH2:19][C:20](Cl)=[O:21]>C(Cl)Cl.O>[CH:1]1([C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[NH:8][C:20](=[O:21])[CH2:19][Cl:18])[CH2:5][CH2:4][CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 130038212-(Cyclopent-2-en-1-yl)aniline

Product 1

HCID 14880661N-[2-(cyclopent-2-enyl)phenyl]-2-chloroacetamideYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 10.00 g (62.8 mmol) of 2-(cyclopent-2-enyl)aniline from Example 1 in 150 mL of methylene chloride and 5.28 g (62.8 mmol) of sodium bicarbonate in 15 mL of water were combined with rapid stirring and cooled 0° C. with the aid of an ice bath. A solution of 7.099 (62.8 mmol) of chloroacetyl chloride in 25 mL of methylene chloride was then added dropwise through the course of 20 min. After an additional hour of vigorous stirring. the layers were separated and the organic layer was dried over anhydrous magnesium sulfate. Evaporation of the solvent in the organic layer and recrystallization of the precipitate with ether afforded 11.41 g (77% yield) of N-[2-(cyclopent-2-enyl)phenyl]-2-chloroacetamide: mp 101°-102° C.

Workup

  1. waitAfter an additional hour of vigorous stirring
  2. customthe layers were separated
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. customEvaporation of the solvent
  5. customin the organic layer and recrystallization of the precipitate with ether

Sources & evidence

ORD record
ord-4ea925b683c14e699ce15b20468eeb3f
Source dataset
uspto-grants-1990_06
Patent number
US04935053

Reaction notes

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