Dimethylformamide → HCID 86750220, compound

HRID 234663Notes

Reaction equation

HRID 234663 reaction equation
N[C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])=[CH:9][C:8]([Cl:19])=[CH:7][CH:6]=2.[CH3:20][S:21][C:22]1[C:27]([N:28]=[C:29]=[O:30])=[C:26]([S:31][CH3:32])[CH:25]=[C:24]([CH3:33])[N:23]=1.C[N:35](C)C=O>C(OCC)(=O)C>[CH3:20][S:21][C:22]1[C:27]([NH:28][C:29](=[O:30])[NH:35][C:3]2[CH:2]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([Cl:19])[CH:9]=3)[N:4]=2)=[C:26]([S:31][CH3:32])[CH:25]=[C:24]([CH3:33])[N:23]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 10017021HCID 10017021, compoundHCID 19597845HCID 19597845, compound

Product 1

HCID 86750220HCID 86750220, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-amino-6-chloro-4-(2-chlorophenyl)quinoline (174 mg, 0.6 mmol) and 2,4-bis(methylthio)-6-methylpyridin-3-yl isocyanate (136 mg, 0.6 mmol) in 3 ml dimethylformamide was heated at 80° C. under nitrogen overnight. The reaction mixture was then cooled to room temperature, diluted with 30 ml ethyl acetate and washed with 2×30 ml water, 30 ml brine, dried (anhydrous sodium sulfate), filtered and concentrated in vacuo. The solid residue was triturated with 10 ml 4:1 hexane/ethyl acetate and filtered to yield the title compound as a white solid (140 mg, 45% yield).

Workup

  1. washwashed with 2×30 ml water, 30 ml brine
  2. dry with materialdried (anhydrous sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe solid residue was triturated with 10 ml 4:1 hexane/ethyl acetate
  6. filtrationfiltered

Sources & evidence

ORD record
ord-1957353607d7472ab33fe2287845578d
Source dataset
uspto-grants-1997_01
Patent number
US05596001

Reaction notes

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