Dimethyl Sulfoxide → HCID 11730404, compound

HRID 430051Notes

Reaction equation

HRID 430051 reaction equation
CS(C)=O.[OH-:5].[K+].[CH2:7]([O:14][C:15]1[CH:20]=[C:19](F)[CH:18]=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O>[CH2:7]([O:14][C:15]1[CH:20]=[C:19]([O:5][C:19]2[CH:18]=[CH:17][C:16]([N+:22]([O-:24])=[O:23])=[C:15]([O:14][CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:20]=2)[CH:18]=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 14797Potassium HydroxideHCID 110969082-(Benzyloxy)-4-fluoro-1-nitrobenzene

Product 1

HCID 11730404HCID 11730404, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

400 g of dimethyl sulfoxide and a solution of 37 g of potassium hydroxide (0.66 mol) in 400 ml:of water are warmed to 100° C. in a three-neck flask fitted with reflux condenser and stirrer. 163 g of the 5-fluoro-2-nitrophenyl benzyl ether prepared as described in Example 1 (0.66 mol) are then added in portions, and the mixture is then heated at 100° C. for 8 hours. After the mixture has been cooled to room temperature, a colorless reaction product precipitates; this is filtered off, washed with water and dried. The reaction product is then recrystallized from ethyl acetate.

Workup

  1. customfitted
  2. temperaturewith reflux condenser and stirrer
  3. additionare then added in portions
  4. temperatureAfter the mixture has been cooled to room temperature
  5. customa colorless reaction product precipitates
  6. filtrationthis is filtered off
  7. washwashed with water
  8. customdried
  9. customThe reaction product is then recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-2d4b187b984c41cfbba99429f4e1419a
Source dataset
uspto-grants-2001_11
Patent number
US06320081B1

Reaction notes

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