Water → HCID 15135634, compound

HRID 359483Notes

Reaction equation

HRID 359483 reaction equation
[NH2:1][C:2]1[C:7]([C:8](=[O:14])[C:9]2[S:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.N1C=CC=CC=1.[O:21]=[C:22]1[CH2:26][CH2:25][CH2:24][N:23]1[CH2:27][CH2:28][CH2:29][C:30](Cl)=[O:31].O>ClCCl>[O:21]=[C:22]1[CH2:26][CH2:25][CH2:24][N:23]1[CH2:27][CH2:28][CH2:29][C:30]([NH:1][C:2]1[C:7]([C:8](=[O:14])[C:9]2[S:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][N:3]=1)=[O:31]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 12711132HCID 12711132, compoundHCID 15135633HCID 15135633, compound

Product 1

HCID 15135634HCID 15135634, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 10 ml of dichloromethane are added 1.02 g of 2-amino-3-(2-thenoyl)pyridine and 0.48 ml of pyridine, whereto a solution of 1.1 g of 4-(2-oxopyrrolidin-1-yl)butyryl chloride in 5 ml of dichloromethane is added dropwise under ice-cooling. The mixture is stirred at room temperature for 2 hours. After the completion of the reaction, water is added to the reaction mixture. The dichloromethane layer is washed with water, and then the solvent is distilled off. The residue is recrystallized from a mixed solvent of ethyl acetate and ethanol to give 2-[4-(2-oxopyrrolidin-1-yl)butyrylamino]-3-(2-thenoyl)pyridine, m.p. 149°-151° C.

Workup

  1. additionis added dropwise under ice-
  2. temperaturecooling
  3. additionis added to the reaction mixture
  4. washThe dichloromethane layer is washed with water
  5. distillationthe solvent is distilled off
  6. customThe residue is recrystallized from a mixed solvent of ethyl acetate and ethanol

Sources & evidence

ORD record
ord-7d2478d475d9492d8ff23149cd5d735a
Source dataset
uspto-grants-1991_03
Patent number
US05001137

Reaction notes

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