Chloroacetyl chloride → HCID 59430654, compound

HRID 506128Notes

Reaction equation

HRID 506128 reaction equation
[CH:1]1([NH:4][C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=2)[CH2:3][CH2:2]1.[OH-].[K+].[Cl:15][CH2:16][C:17](Cl)=[O:18]>CCOC(C)=O>[Cl:15][CH2:16][C:17]([N:4]([CH:1]1[CH2:3][CH2:2]1)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=1)=[O:18]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 14797Potassium HydroxideHCID 45091015N-Cyclopropyl-3-methoxyaniline

Product 1

HCID 59430654HCID 59430654, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of cyclopropyl(3-methoxyphenyl)amine (1.52 g, 9.3 mmol), KOH (1.57 g dissolved in 8 mL H2O) and EtOAc (15 mL) at 0° C. was added dropwise, with vigorous stirring, chloroacetyl chloride (1.12 mL, 14.0 mmol). The mixture was stirred for additional 30 minutes, washed with water (3×350 mL), concentrated and purified on silica gel (CH2Cl2/hexane, 1:1) to provide 2-chloro-N-cyclopropyl-N-(3-methoxy-phenyl)acetamide as a solid (1.80 g, 81%).

Workup

  1. washwashed with water (3×350 mL)
  2. concentrationconcentrated
  3. custompurified on silica gel (CH2Cl2/hexane, 1:1)

Sources & evidence

ORD record
ord-267f1356d1c841259f1669a11868d2fe
Source dataset
uspto-grants-2010_08
Patent number
US07781478B2

Reaction notes

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