Dimethyl Sulfoxide → HCID 12082824, compound

HRID 1941710Notes

Reaction equation

HRID 1941710 reaction equation
Br[CH2:2][C:3]1[C:4]([C:24]([F:27])([F:26])[F:25])=[N:5][N:6]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)[C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.N1C(C)=CC(C)=CC=1C.CS(C)=[O:39]>>[CH:2]([C:3]1[C:4]([C:24]([F:27])([F:26])[F:25])=[N:5][N:6]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)[C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:39]

Participants

4

Reactant 3

HCID 679Dimethyl SulfoxideHCID 79532,4,6-TrimethylpyridineHCID 12150543HCID 12150543, compound

Product 1

HCID 12082824HCID 12082824, compoundYield 66%

Conditions

Temperature
120 °C

Procedure

To a solution of the compound prepared in Step 1 (362 mg, 0.79 mmol) in dimethyl sulfoxide (7 mL) was added collidine (0.14 mL, 1.0 mmol). The solution was heated at 120° C. for 3 hours and then kept at overnight at room temperature. The reaction solution was partitioned between ethyl acetate and water and the organic solution was washed with water, dried and concentrated. The residue was chromatographed (1:1 hexane:ethyl acetate) to give the desired product (205 mg, 66%).

Workup

  1. customThe reaction solution was partitioned between ethyl acetate and water
  2. washthe organic solution was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was chromatographed (1:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-6f1cf560ed8e450d9d3713ae1c50e0ce
Source dataset
uspto-grants-2013_03
Patent number
USRE044048E1

Reaction notes

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