Chloroacetyl chloride → HCID 57742180, compound

HRID 660286Notes

Reaction equation

HRID 660286 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][C:3]=1[OH:15].[Cl:16][CH2:17][C:18](Cl)=[O:19]>CC(C)CC(=O)C.O>[Cl:16][CH2:17][C:18]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][C:3]=1[OH:15])=[O:19]

Participants

5

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 12370790HCID 12370790, compound

Product 1

HCID 57742180HCID 57742180, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of Ethyl 2-(4-amino-3-hydroxyphenyl)propanoate (101 mg, 0.483 mmol) in 4-methyl-2-pentanone (4 mL) was added chloroacetyl chloride (58 mg, 0.514 mmol) in 4-methyl-2-pentanone (2 mL) at room temperature. The reaction mixture was stirred for 12 hrs at 80° C. then cooled to room temperature. The mixture was diluted with H2O and extracted with EtOAc. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes (1:2) as eluant.

Workup

  1. temperaturethen cooled to room temperature
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-6d9ba94bba024f6fba3cf9061514cd10
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Reaction notes

Loading…