Pyridine → HCID 20314376, compound

HRID 1580721Notes

Reaction equation

HRID 1580721 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][CH:15]1[CH2:20][O:19][C:17](=[O:18])[CH2:16]1.N1C=CC=CC=1>C(OCC)(=O)C.O>[Cl:1][CH2:2][C:3]([N:14]([CH:15]1[CH2:20][O:19][C:17](=[O:18])[CH2:16]1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[O:7][CH3:6])=[O:4]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 20554802HCID 20554802, compound

Product 1

HCID 20314376HCID 20314376, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
46 °C

Procedure

A 5.4 g ().044 mol) sample of chloroacetyl chloride was added dropwise to a solution of 9 g (0.044 mol) 3-(N-2-methoxyphenylamino)-γ-butyrolactone and 3.8 g (0.048 mol) pyridine in 150 ml ethyl acetate at 37° to 46°C. After stirring at 46°C for 15 minutes, the reaction mixture was cooled and diluted with water. The organic layer was separated, washed with 10% aqueous sodium bicarbonate, washed with water, dried over magnesium sulfate and evaporated under reduced pressure to give the product, as a colorless solid. The melting point and elemental analysis for the product is tabulated in Table I.

Workup

  1. temperaturethe reaction mixture was cooled
  2. customThe organic layer was separated
  3. washwashed with 10% aqueous sodium bicarbonate
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customto give the product

Sources & evidence

ORD record
ord-638dc41a2df84cab90338262e8bc34f8
Source dataset
uspto-grants-1976_01
Patent number
US03933860

Reaction notes

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