Dimethylformamide → HCID 86605410, compound

HRID 2102326Notes

Reaction equation

HRID 2102326 reaction equation
[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([C:14]2[CH:23]=[CH:22][C:17]3[O:18][CH2:19][CH2:20][O:21][C:16]=3[CH:15]=2)[N:11]([CH:24]([CH3:26])[CH3:25])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+].CN(C)[CH:36]=[O:37]>>[CH2:1]([O:8][C:9]1[NH:10][N:11]([CH:24]([CH3:26])[CH3:25])[C:12]([C:14]2[CH:23]=[CH:22][C:17]3[O:18][CH2:19][CH2:20][O:21][C:16]=3[CH:15]=2)([CH:36]=[O:37])[CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 66970992HCID 66970992, compound

Product 1

HCID 86605410HCID 86605410, compound

Conditions

Temperature
80 °C

Procedure

To a solution of 3-benzyloxy-5-(2,3-dihydrobenzo-[1,4]dioxin-6-yl)-1-isopropyl-1H-pyrazole (1.8 g) in N,N-dimethylformamide (3 mL) was added phosphorus oxychloride (0.97 g) at 80° C., and the mixture was stirred at 80° C. for 2 hours. After the reaction mixture was cooled to room temperature, a sodium hydroxide aqueous solution (2 mol/L, 10 mL) was added to the reaction mixture. The mixture was extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent:hexane/dichloromethane=1/4-dichloromethane) to give the title compound (0.86 g).

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. extractionThe mixture was extracted with diethyl ether
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent:hexane/dichloromethane=1/4-dichloromethane)

Sources & evidence

ORD record
ord-7f43fd95e49e4f7cb0e634d59f4c77ab
Source dataset
uspto-grants-2009_08
Patent number
US07576063B2

Reaction notes

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