Dimethyl Sulfoxide → HCID 12082824, compound

HRID 1292318Notes

Reaction equation

HRID 1292318 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-d55e5e6235b944548a02d25d29a37c82
Source dataset
uspto-grants-1998_05
Patent number
US05756529

Reaction notes

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