Hydrochloric Acid → HCID 13368795, compound

HRID 483096Notes

Reaction equation

HRID 483096 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:3]=1[CH2:4][CH:5]1[CH2:9][C:8](=[O:10])[NH:7][CH:6]12.[H-].[Na+].Cl[CH2:18][C:19]([NH2:21])=[O:20].Cl>CN(C)C=O>[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:3]=1[CH2:4][CH:5]1[CH2:9][C:8](=[O:10])[N:7]([CH2:18][C:19]([NH2:21])=[O:20])[CH:6]12

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6580ChloroacetamideHCID 24758Sodium hydrideHCID 13368792HCID 13368792, compound

Product 1

HCID 13368795HCID 13368795, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2.7 g of 5-chloro-1,2,3,3a,4,8b-hexahydro-indeno[1,2-b]pyrrol-2-one in 80 ml of dimethylformamide is added 0.8 g of sodium hydride (60% dispersion in mineral oil). After the evolution of gas ceases, the mixture is heated at 50°-60° C. for 1 hour whereupon a solution of 1.8 g of monochloroacetamide in 30 ml of dimethylformamide is added dropwise, and the resulting mixture is stirred at the same temperature for 2 hours and then cooled. The reaction mixture is poured into ice-cold water, acidified with dilute hydrochloric acid and extracted with chloroform. The extract is dried over sodium sulfate, and the solvent is distilled off. The residue is crystallized with a mixture of acetone and ether. The crystalline product is collected by suction filtration and recrystallized from ether to give 1.4 g of [5-chloro-1,2,3,3a,4,8b-hexahydro-2-oxo-indeno[1,2-b]pyrrol-1-yl]acetamide, melting at 186°-188° C.

Workup

  1. additionis added dropwise
  2. temperaturecooled
  3. additionThe reaction mixture is poured into ice-cold water
  4. extractionextracted with chloroform
  5. dry with materialThe extract is dried over sodium sulfate
  6. distillationthe solvent is distilled off
  7. customThe residue is crystallized with a mixture of acetone and ether
  8. filtrationThe crystalline product is collected by suction filtration
  9. customrecrystallized from ether

Sources & evidence

ORD record
ord-2b7cd27b6b5848b9820490918e467b76
Source dataset
uspto-grants-1986_03
Patent number
US04578397

Reaction notes

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