2,4,6-Trimethylphenyl isothiocyanate → 1-[4-(Dipropylamino)pyridin-2-yl]-3-mesitylthiourea

HRID 2235489Notes

Reaction equation

HRID 2235489 reaction equation
[CH2:1]([N:4]([CH2:12][CH2:13][CH3:14])[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH2:11])[CH:6]=1)[CH2:2][CH3:3].[C:15]1([CH3:26])[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:16]=1[N:23]=[C:24]=[S:25]>CO.O>[CH2:12]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:24]([NH:23][C:16]2[C:15]([CH3:26])=[CH:20][C:19]([CH3:21])=[CH:18][C:17]=2[CH3:22])=[S:25])[CH:6]=1)[CH2:13][CH3:14]

Participants

5

Reactant 2

HCID 1386592,4,6-Trimethylphenyl isothiocyanateHCID 86049193HCID 86049193, compound

Product 1

HCID 860491941-[4-(Dipropylamino)pyridin-2-yl]-3-mesitylthioureaYield 22%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To 0.106 g (0.0.55 mmol) of N4,N4-dipropylpyridine-2,4-diamine in 10 mL of methanol was added 0.117 g (0.66 mmol) of mesitylisothiocyanate. The mixture was heated at reflux for 24 h, diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, concentrated in vacuo and the resulting crude solid was purified by flash chromatography eluting with a 85% hexanes/ethyl acetate mixture to give 0.044 g (22%) of the title compound as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 24 h
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customthe resulting crude solid was purified by flash chromatography
  9. washeluting with a 85% hexanes/ethyl acetate mixture

Sources & evidence

ORD record
ord-9a297eaa121342cf922b4782325c90a2
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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