Allyl chloride → [4-(Acryloylmethylamino)phenyl]acetic Acid Methyl Ester

HRID 1097074Notes

Reaction equation

HRID 1097074 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH3:12])=[CH:7][CH:6]=1.[CH:14](N(CC)C(C)C)([CH3:16])[CH3:15].C(Cl)C=C.C(=O)(O)[O-:28].[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH2:12][C:15](=[O:28])[CH:14]=[CH2:16])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 7850Allyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 15892780Methyl 2-(4-(methylamino)phenyl)acetate

Product 1

HCID 66770363[4-(Acryloylmethylamino)phenyl]acetic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl(4-methylaminophenyl)acetate (4.00 g, 22.3 mmol) and N,N-diisopropylethylamine (7.78 mL, 44.6 mmol) in DCM (20.0 mL) at 0° C. was slowly added 2-propenyl chloride (2.18 mL, 26.8 mmol). The reaction mixture was stirred at room temperature for 2 h and then saturated aqueous sodium bicarbonate (20.0 mL) was added. This mixture was extracted with DCM (10 mL) and the organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound, which was used in the next reaction without further purification.

Workup

  1. customat 0° C.
  2. extractionThis mixture was extracted with DCM (10 mL)
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2e9913742360498bbec166cd0bd5e362
Source dataset
uspto-grants-2012_03
Patent number
US08138345B2

Reaction notes

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