Formamide → HCID 85956452, compound

HRID 917665Notes

Reaction equation

HRID 917665 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=O)=[CH:9][C:4]=2[O:3][CH2:2]1.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([OH:21])=[O:20])=[CH:15][CH:14]=1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.C(=O)([O-])O.[Na+].[CH:42]([NH2:44])=[O:43]>CCCCCC.C(OCC)(=O)C.O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([S:19]([C:16]3[CH:17]=[CH:18][C:13]([CH3:12])=[CH:14][CH:15]=3)(=[O:21])=[O:20])[NH:44][CH:42]=[O:43])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

9

Reactant 5

HCID 713FormamideHCID 8438PiperonalHCID 10818p-Toluenesulfinic acidHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 516892Sodium Bicarbonate

Product 1

HCID 85956452HCID 85956452, compoundYield 33%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of benzo[1,3]dioxole-5-carbaldehyde (1.0 g, 6.66 mmol), 4-methyl-benzenesulfinic acid (1.1 g, 7.24 mmol, 1.09 equiv), and 10-camphorsulfonic acid (0.4 g, 1.72 mmol, 0.25 equiv) in formamide (2.8 mL) was heated to 75° C. for four hours. The resulting reaction mixture was cooled to ambient temperature, poured into a mixture of saturated aqueous sodium hydrogen carbonate (100 mL), water (100 mL), ethyl acetate (20 mL) and hexane (20 mL), and stirred at ambient temperature for 20 minutes. The resulting white solid was filtered off and azeotroped with toluene (2×50 mL) to provide N-[Benzo[1,3]dioxol-5-yl-(toluene-4-sulfonyl)-methyl]-formamide (740 mg, 33%).

Workup

  1. customThe resulting reaction mixture
  2. filtrationThe resulting white solid was filtered off
  3. customazeotroped with toluene (2×50 mL)

Sources & evidence

ORD record
ord-3dd22281421445758a1629bfa7138d7a
Source dataset
uspto-grants-2007_09
Patent number
US07273936B2

Reaction notes

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