Dimethyl Sulfoxide → HCID 87845586, compound

HRID 1664100Notes

Reaction equation

HRID 1664100 reaction equation
[N-]=[N+]=[N-].[Na+].[F:5][C:6]1([F:24])[O:11][C:10]2[CH:12]=[CH:13][C:14]([C:16]([C:18](Br)([CH3:20])[CH3:19])=[O:17])=[CH:15][C:9]=2[O:8][C:7]1([F:23])[F:22].CS(C)=O>O>[F:5][C:6]1([F:24])[O:11][C:10]2[CH:12]=[CH:13][C:14]([C:16]([C:18]3[CH:20]=[CH:15][C:9]4[O:8][C:7]([F:23])([F:22])[C:6]([F:5])([F:24])[O:11][C:10]=4[CH:19]=3)=[O:17])=[CH:15][C:9]=2[O:8][C:7]1([F:23])[F:22]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 33557Sodium AzideHCID 87152141HCID 87152141, compound

Product 1

HCID 87845586HCID 87845586, compoundYield 136.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.65 g of sodium azide was added to a mixture comprising 1.78 g of α-bromoisopropyl 2,2,3,3-tetrafluoro-1,4-benzodioxan-6-yl ketone and 10 ml of dimethyl sulfoxide, followed by a reaction for two hours at 50° C. The reaction mixture was put into water, and extracted with diethyl ether, followed by washing with water. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/n-hexane=1/19) to obtain 1.5 g of oily α-azideisopropyl 2,2,3,3-tetrafluoro-1,4-benzodioxan-6-yl ketone. The NMR spectrum data of this product is as follows.

Workup

  1. customfollowed by a reaction for two hours at 50° C
  2. extractionextracted with diethyl ether
  3. washby washing with water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/n-hexane=1/19)

Sources & evidence

ORD record
ord-7ea08995b0464259a32145768cf93582
Source dataset
uspto-grants-2011_10
Patent number
US08039420B2

Reaction notes

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