HCID 19597845, compound → HCID 19597974, compound

HRID 611630Notes

Reaction equation

HRID 611630 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:9][NH2:10].[CH3:15][S:16][C:17]1[C:22]([N:23]=[C:24]=[O:25])=[C:21]([S:26][CH3:27])[CH:20]=[C:19]([CH3:28])[N:18]=1>CN(C)C=O.C(OCC)(=O)C>[CH3:15][S:16][C:17]1[C:22]([NH:23][C:24]([NH:10][CH2:9][CH:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])[CH2:11][CH2:12][CH2:13][CH3:14])=[O:25])=[C:21]([S:26][CH3:27])[CH:20]=[C:19]([CH3:28])[N:18]=1

Participants

5

Reactant 2

HCID 19597845HCID 19597845, compoundHCID 19597938HCID 19597938, compound

Product 1

HCID 19597974HCID 19597974, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(2-methylphenyl)hexylamine (153 mg, 0.8 mmol) and 2,4-bis(methylthio)-6-methylpyridin-3-yl isocyanate (180 mg, 0.8 mmol) in 3 ml dimethylformamide was heated at 80° C. under nitrogen overnight. The reaction mixture was cooled to room temperature and diluted with 60 ml ethyl acetate. The resulting solution was washed sequentially with 3×50 ml water and 50 ml brine, dried (sodium sulfate), filtered and concentrated in vacuo. The residue was chromatographed on silica gel (200 g), eluting with 7:3 hexane/ethyl acetate to yield the title compound as a white solid (110 mg, 33% yield).

Workup

  1. washThe resulting solution was washed sequentially with 3×50 ml water and 50 ml brine
  2. dry with materialdried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel (200 g)
  6. washeluting with 7:3 hexane/ethyl acetate

Sources & evidence

ORD record
ord-7ac33a5d30d943a78b7bee3b797f4665
Source dataset
uspto-grants-1999_12
Patent number
US06001860

Reaction notes

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