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

HRID 1055351Notes

Reaction equation

HRID 1055351 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.C(N(CC)C(C)C)(C)C.[C:23](Cl)(=[O:26])[CH:24]=[CH2:25].C(=O)(O)[O-].[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:23](=[O:26])[CH:24]=[CH2:25])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 13140Acryloyl 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-propenoyl 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-ce8cb3f0ab294268b6858b68b935e524
Source dataset
uspto-grants-2016_07
Patent number
US09394275B2

Reaction notes

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