Diiodomethane → HCID 10002310, compound

HRID 1905427Notes

Reaction equation

HRID 1905427 reaction equation
C(I)I.[C:4](=O)([O-])[O-].[K+].[K+].[C:10]([N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:28]=[C:27]3[C:22]([C:23]([OH:35])=[C:24]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:25]([SH:29])=[N:26]3)=[CH:21][C:20]=2[Cl:36])[CH2:15][CH2:14]1)(=[O:12])[CH3:11]>CN(C)C=O>[C:10]([N:13]1[CH2:14][CH2:15][N:16]([C:19]2[CH:28]=[C:27]3[C:22]([C:23](=[O:35])[C:24]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:25]4[S:29][CH2:4][N:26]43)=[CH:21][C:20]=2[Cl:36])[CH2:17][CH2:18]1)(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 6346DiiodomethaneHCID 11430Potassium CarbonateHCID 178470131HCID 178470131, compound

Product 1

HCID 10002310HCID 10002310, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Into 50 ml of N,N-dimethylformamide were placed 2.35 g of methylene iodide and 2.5 g of potassium carbonate and a solution of 3.0 g of ethyl 7-(4-acetyl-1-piperazinyl)-6-chloro-4-hydroxy-2-mercaptoquinoline-3-carboxylate in 30 ml of N,N-dimethylformamide was gradually dropped in with stirring. After that, the mixture was stirred at room temperature for 1 hour, concentrated in vacuo, water was added to the residue, and insoluble crystals were collected by filtration. They were washed with water, dried, and recrystallized from a mixed solvent of ethanol and chloroform to give 2.49 g of colorless powdery crystals, m.p. 266°-268° C. (decompn).

Workup

  1. stirringAfter that, the mixture was stirred at room temperature for 1 hour
  2. concentrationconcentrated in vacuo, water
  3. additionwas added to the residue, and insoluble crystals
  4. filtrationwere collected by filtration
  5. washThey were washed with water
  6. customdried
  7. customrecrystallized from a mixed solvent of ethanol and chloroform

Sources & evidence

ORD record
ord-ffa9ad5a18dd4de0ae26e410eb06d054
Source dataset
uspto-grants-1989_06
Patent number
US04843070

Reaction notes

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