Tert-Butyl nitrite → HCID 25234838, compound

HRID 1930274Notes

Reaction equation

HRID 1930274 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[C:13]([N:23]4[CH:28]=[CH:27][C:26](=[O:29])[NH:25][C:24]4=[O:30])[CH:14]=[C:15]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:16]=3[O:17][CH3:18])[CH:8]=[CH:7][C:5]=2[N:6]=1.N(O[C:34](C)([CH3:36])[CH3:35])=O>C(#N)C.[Cu](Cl)Cl>[C:19]([C:15]1[CH:14]=[C:13]([N:23]2[CH:28]=[CH:27][C:26](=[O:29])[NH:25][C:24]2=[O:30])[CH:12]=[C:11]([C:9]2[CH:8]=[CH:7][C:5]3[N:6]=[C:2]([NH:1][CH2:35][CH2:34][CH3:36])[S:3][C:4]=3[CH:10]=2)[C:16]=1[O:17][CH3:18])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 25234760HCID 25234760, compound

Product 1

HCID 25234838HCID 25234838, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of the product from Example 53 (50 mg, 0.118 mmol) and copper(II) chloride (24 mg, 0.178 mmol) in acetonitrile (3 mL) at 0° C. was added tert-butyl nitrite (21 μL, 0.178 mmol). The mixture was stirred at 0° C. for 1 h, and then warmed to 65° C. and stirred for 2 h. The mixture was concentrated in vacuo and purified by column chromatography on silica gel using 5% MeOH in CH2Cl2 to give the title compound as an off-white solid (43 mg, 82%).

Workup

  1. temperaturewarmed to 65° C.
  2. stirringstirred for 2 h
  3. concentrationThe mixture was concentrated in vacuo
  4. custompurified by column chromatography on silica gel using 5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-dc16f1a36f6d47efbe3da66e8e2f5408
Source dataset
uspto-grants-2012_05
Patent number
US08188104B2

Reaction notes

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