Dimethyl Sulfoxide → HCID 90014581, compound

HRID 1484508Notes

Reaction equation

HRID 1484508 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([CH3:3])C.[CH3:11]S(C)=O.Cl[C:16]1[C:21]([CH3:22])=[CH:20][C:19]([N+:23]([O-:25])=[O:24])=[CH:18][N:17]=1>>[CH3:22][C:21]1[C:16]([O:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([CH2:1][CH2:3][CH3:11])[CH:5]=2)=[N:17][CH:18]=[C:19]([N+:23]([O-:25])=[O:24])[CH:20]=1

Participants

4

Reactant 3

HCID 679Dimethyl SulfoxideHCID 120593-IsopropylphenolHCID 896482-Chloro-3-methyl-5-nitropyridine

Product 1

HCID 90014581HCID 90014581, compoundYield 88.3%

Conditions

Temperature
20 °C

Procedure

To a solution of 3-isopropylphenol (174 mg, 1.28 mmol) in DMSO (5 mL) tBuOK (143 mg, 1.28 mmol) was added and the reaction mixture was stirred at 20° C. for 30 mins. 2-chloro-3-methyl-5-nitropyridine (200 mg, 1.16 mmol) was added and the resulting mixture was stirred at 120° C. for 2 hrs. The reaction mixture was cooled to r. t., poured into ice-water (20 ml) and extracted with DCM (3×50 mL). The combined organic layer was dried over Na2SO4, filtered and concentrated to afford the title compound (279 mg) as a light red oil.

Workup

  1. stirringthe resulting mixture was stirred at 120° C. for 2 hrs
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with DCM (3×50 mL)
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-12896af48b8746c1879f333125ea8df5
Source dataset
uspto-grants-2016_08
Patent number
US09422252B2

Reaction notes

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