Tert-Butyl nitrite → HCID 22598267, compound

HRID 1369351Notes

Reaction equation

HRID 1369351 reaction equation
[OH:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH2:5][CH2:4][C:3]1([CH3:11])[CH3:10].N(OC(C)(C)C)=O.[C:19]([C:23]1[CH:24]=[C:25]([CH:27]=[C:28]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:29]=1)N)([CH3:22])([CH3:21])[CH3:20]>N1C=CC=CC=1>[C:19]([C:23]1[CH:24]=[C:25]([CH:27]=[C:28]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:29]=1)[O:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH2:5][CH2:4][C:3]1([CH3:11])[CH3:10])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 754193,5-Di-tert-butylanilineHCID 5499762,2,6,6-Tetramethylpiperidin-1-ol

Product 1

HCID 22598267HCID 22598267, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The procedure of Example 1 is repeated using 1.50 g (9.6 mmol) of 1-oxyl-2,2,6,6-tetramethylpiperidine, 2.38 g (24 mmol) of tert-butyl nitrite, 5.8 mg (0.0096 mmol) of (S,S)-(+)-N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II), 90 mL of pyridine and 3.93 g (19.2 mmol) of 3,5-di-tert-butylaniline at 70° C. The crude product obtained is purified by vacuum flash chromatography (heptane) to give 2.8 g of the title compound as an off-white solid in 84.8% yield. The structure is confirmed by 1Hnmr and elemental analysis.

Workup

  1. customat 70° C
  2. customThe crude product obtained
  3. customis purified by vacuum flash chromatography (heptane)

Sources & evidence

ORD record
ord-ce288f88f1334583b1c5a6a562ea8a93
Source dataset
uspto-grants-2003_06
Patent number
US06579328B2

Reaction notes

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