Water → 4-Acetamidophenyl chloroacetate

HRID 921995

Reaction equation

HRID 921995 reaction equation
[NH:1]([C:5]1[CH:11]=[CH:10][C:8]([OH:9])=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3].N1C=CC=CC=1.[Cl:18][CH2:19][C:20](Cl)=[O:21].O>CC(C)=O>[Cl:18][CH2:19][C:20]([O:9][C:8]1[CH:10]=[CH:11][C:5]([NH:1][C:2](=[O:3])[CH3:4])=[CH:6][CH:7]=1)=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 1983AcetaminophenHCID 6577Chloroacetyl chloride

Product 1

HCID 132776644-Acetamidophenyl chloroacetateYield 72%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

Paracetamol [1] (15.117 g, 50 mmol) and pyridine (7.910 g, 50 mmol) were suspended in anhydrous acetone (200 ml) and chilled to 0° C. under an atmosphere of dry nitrogen. Chloroacetylchloride (11.29 g, 50 mmol) was added dropwise (violent reaction) and the resulting solution was stirred for additional 2 hours at room temperature. Water (300 ml) was added and the mixture was heated until a clear solution was obtained. The product [2] precipitated upon cooling and was collected via filtration, washed with water and dried under reduced pressure (0.01 mbar, 50° C.) to yield [2] as colourless needles in 72% yield. The product was pure according to 1H NMR and directly subjected to the next step without further purification.

Workup

  1. custom(violent reaction)
  2. temperaturethe mixture was heated until a clear solution
  3. customwas obtained
  4. customThe product [2] precipitated
  5. temperatureupon cooling
  6. filtrationwas collected via filtration
  7. washwashed with water
  8. customdried under reduced pressure (0.01 mbar, 50° C.)

Sources & evidence

ORD record
ord-f2cfd49c4d054b0dbf6cf00557457071
Source dataset
uspto-grants-2016_03
Patent number
US09278134B2

Linked notes

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