Tert-Butyl nitrite → HCID 58624929, compound

HRID 1013427Notes

Reaction equation

HRID 1013427 reaction equation
C(ON=O)(C)(C)C.[CH2:8]([O:10][C:11]([C:13]1[C:24]2[CH:23]3[CH:19]([CH2:20][N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:22]3)[CH2:18][CH2:17][C:16]=2[S:15][C:14]=1N)=[O:12])[CH3:9]>C(O)C.O.C([O-])(=O)C.C([O-])(=O)C.[Cu+2]>[CH2:8]([O:10][C:11]([C:13]1[C:24]2[CH:23]3[CH:19]([CH2:20][N:21]([C:25]([O:27][C:28]([CH3:29])([CH3:31])[CH3:30])=[O:26])[CH2:22]3)[CH2:18][CH2:17][C:16]=2[S:15][CH:14]=1)=[O:12])[CH3:9]

Participants

6

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 58624935HCID 58624935, compound

Product 1

HCID 58624929HCID 58624929, compoundYield 36%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Tert-butylnitrite (7.09 g, 0.069 mol) was added to the product of step d) (16.8 g, 0.046 mol) dissolved in 200 mL of ethanol followed by the addition of copper diacetate (12.5 g, 0.069 mol). The reaction mixture was heated for one hour at 60° C., cooled to room temperature, diluted with 200 mL of water and extracted with ethyl acetate (3×200 mL). The combined organic extracts were dried (MgSO4) and solvent evaporated in vacuo to give the crude product that was purified by column chromatography (SiO2) using a 5-50% ethylacetate-hexane gradient to afford the subtitle compound (5.8 g, yield: 36%). MS calculated for C18H25NO4S +H: 352, observed: 352.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate (3×200 mL)
  3. dry with materialThe combined organic extracts were dried (MgSO4) and solvent
  4. customevaporated in vacuo
  5. customto give the crude product that
  6. customwas purified by column chromatography (SiO2)

Sources & evidence

ORD record
ord-3bb90273b73348a48c7bbb12cb7c75ca
Source dataset
uspto-grants-2011_07
Patent number
US07981919B2

Reaction notes

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