Pyridine → HCID 20314376, compound

HRID 596949Notes

Reaction equation

HRID 596949 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 (0.044 mol) sample of chloroacetyl chloride was added dropwise to a solution of 9 g (0.044 mol) 3-(N-2-methoxyphenylamino)-gamma-butyrolactone and 3.8 g (0.048mol) pyridine in 150 ml ethyl acetate at 37°-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, as compound No. 3.

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-e206e273133d4391b32470b5374fdcc2
Source dataset
uspto-grants-1977_03
Patent number
US04012519

Reaction notes

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