Dimethylformamide → HCID 70873547, compound

HRID 2172181Notes

Reaction equation

HRID 2172181 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]([OH:37])([CH3:36])[CH2:23][CH2:24]OS(C3C=CC(C)=CC=3)(=O)=O)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:38][C:39]1[NH:40][CH:41]=[C:42]([N+:44]([O-:46])=[O:45])[N:43]=1.C(=O)([O-])O.[Na+].CN(C)C=O>O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]([OH:37])([CH3:36])[CH2:23][CH2:24][N:40]3[CH:41]=[C:42]([N+:44]([O-:46])=[O:45])[N:43]=[C:39]3[Cl:38])=[CH:16][CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 86709367HCID 86709367, compoundHCID 178526855HCID 178526855, compound

Product 1

HCID 70873547HCID 70873547, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

4-{4-[2-Hydroxy-2-methyl-4-(toluene-4-sulfonyloxy)butoxy]phenyl}piperazine-1-carboxylic acid tert-butyl ester (4.69 g, 8.77 mmol), 2-chloro-4-nitro-1H-imidazole (1.55 g, 10.52 mmol), sodium hydrogen carbonate (0.88 g) and dimethylformamide (47 ml) were mixed, and the mixture was stirred at 90 to 100° C. overnight. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution, and dried over magnesium sulfate. After filtering under reduced pressure, the filtrate was concentrated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:0→3:7) to afford the title compound as a yellow amorphous solid (2.12 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationAfter filtering under reduced pressure
  5. concentrationthe filtrate was concentrated
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:0→3:7)

Sources & evidence

ORD record
ord-978cd0bc9e684e958ff5e8b1894a115d
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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