Phenyl isocyanate → HCID 86591451, compound

HRID 1727361Notes

Reaction equation

HRID 1727361 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[N:9]=[C:10]([NH2:20])[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=2)[CH:5]=[C:4]([CH3:21])[N:3]=1.[C:22]1([N:28]=[C:29]=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])O.[Na+]>CN(C)C(=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[N:9]=[C:10]([NH:20][C:29]([NH:28][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:30])[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=2)[CH:5]=[C:4]([CH3:21])[N:3]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 516892Sodium BicarbonateHCID 22932696HCID 22932696, compound

Product 1

HCID 86591451HCID 86591451, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of [4-(2,6-dimethyl-4-pyridyl)-5-(3-methylphenyl)-1,3-thiazol-2-yl]amine (0.50 g, 1.7 mmol) in N,N-dimethylacetamide (20 mL) was added phenyl isocyanate (0.28 mL, 2.6 mmol), and the mixture was stirred for 14 hours at 80° C. Aqueous sodium hydrogen carbonate was poured into the reaction mixture, and extracted with ethyl acetate. The extracts were washed with brine, then, dried to be concentrated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=1:1). The resulted crude crystal was recrystallized from ethyl acetate-hexane to obtain a title compound (0.34 g, yield 48%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with brine
  3. customdried
  4. concentrationto be concentrated
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate=1:1)
  6. customThe resulted crude crystal
  7. customwas recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-61d5c4fe387f411781cf996803d3c0fa
Source dataset
uspto-grants-2009_02
Patent number
US07495018B2

Reaction notes

Loading…