2,6-Lutidine → 5-[Isocyano(4-methylbenzene-1-sulfonyl)methyl]-2H-1,3-benzodioxole

HRID 917666Notes

Reaction equation

HRID 917666 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[NH:11][CH:12]=O)=[CH:9][C:4]=2[O:3][CH2:2]1.P(Cl)(Cl)(Cl)=O.N1C(C)=CC=CC=1C.C(=O)([O-])O.[Na+]>C1COCC1>[N+:11]([CH:10]([S:14]([C:17]1[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=1)(=[O:16])=[O:15])[C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH2:2][O:3][C:4]=2[CH:9]=1)#[C-:12]

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 85956452HCID 85956452, compound

Product 1

HCID 27717375-[Isocyano(4-methylbenzene-1-sulfonyl)methyl]-2H-1,3-benzodioxoleYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[benzo[1,3]dioxol-5-yl-(toluene-4-sulfonyl)-methyl]-formamide (740 mg, 2.22 mmol) in THF (50 mL) was slowly added phosphorous oxychloride (0.41 mL, 4.44 mmol, 2 equiv). The resulting reaction mixture was stirred at ambient temperature for 2 hours, cooled to 0° C. and slowly treated with 2,6-lutidine (1.55 mL, 13.32 mmol, 6 equiv). The reaction mixture was stirred at ambient temperature for 48 hours, treated with saturated aqueous sodium hydrogen carbonate (80 mL), and then extracted with ethyl acetate (50 mL). The organics were dried over magnesium sulfate and concentrated in vacuo. Silica gel chromatography (20% ethyl acetate in hexane) provided 5-[Isocyano-(toluene4-sulfonyl)-methyl]-benzo[1,3]dioxole as a white solid (200 mg, 29%).

Workup

  1. customThe resulting reaction mixture
  2. temperaturecooled to 0° C.
  3. stirringThe reaction mixture was stirred at ambient temperature for 48 hours
  4. extractionextracted with ethyl acetate (50 mL)
  5. dry with materialThe organics were dried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-acbfe47a50cc48e7950ebce023c8ef43
Source dataset
uspto-grants-2007_09
Patent number
US07273936B2

Reaction notes

Loading…