Chlorosuccinimide → Ethyl 2-(4-amino-3-chloro-5-(cyclopropylmethoxy)phenyl)acetate

HRID 1183735Notes

Reaction equation

HRID 1183735 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][C:3]=1[O:14][CH2:15][CH:16]1[CH2:18][CH2:17]1.C1C(=O)N([Cl:26])C(=O)C1>C(Cl)(Cl)(Cl)Cl.O>[NH2:1][C:2]1[C:3]([O:14][CH2:15][CH:16]2[CH2:18][CH2:17]2)=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][C:7]=1[Cl:26]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 57995628Ethyl 2-(4-amino-3-(cyclopropylmethoxy)phenyl)acetate

Product 1

HCID 57995503Ethyl 2-(4-amino-3-chloro-5-(cyclopropylmethoxy)phenyl)acetateYield 101.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred solution of ethyl 2-(4-amino-3-(cyclopropylmethoxy)phenyl)acetate (1.2 g, 4.0 mmol) in dry CCl4 (60 mL), NCS (0.427 g, 3.2 mmol) was added at 0° C. The reaction mixture was allowed to stir for 3 h at room temperature to complete the reaction. The reaction mixture was diluted with water, extracted with DCM (2×50 mL), the combined organic solvents was dried over Na2SO4, filtered and concentrated in vacuo. The crude reaction mixture was purified by column chromatography to yield Ethyl 2-(4-amino-3-chloro-5-(cyclopropylmethoxy)phenyl)acetate (920 mg) as a yellow solid.

Workup

  1. customthe reaction
  2. extractionextracted with DCM (2×50 mL)
  3. dry with materialthe combined organic solvents was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude reaction mixture
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-16249264aab649dabf369708b692acf0
Source dataset
uspto-grants-2014_03
Patent number
US08664249B2

Reaction notes

Loading…