tert-Butyl hydroperoxide → HCID 67609461, compound

HRID 2196248Notes

Reaction equation

HRID 2196248 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@@:11]2([CH3:18])[NH:16][C:15](=S)[CH2:14][O:13][CH2:12]2)[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.C(OO)(C)(C)C.[OH-].[NH3:26].[O-]S([O-])(=S)=O.[Na+].[Na+]>N.CO>[Br:1][C:2]1[CH:3]=[C:4]([C@:11]2([CH3:18])[CH2:12][O:13][CH2:14][C:15]([NH2:26])=[N:16]2)[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

7

Reactant 4

HCID 6410tert-Butyl hydroperoxideHCID 24477Sodium ThiosulfateHCID 21862953Ammonia hydroxideHCID 86667520(R)-5-(3-Bromo-5-nitro-phenyl)-5-methyl-morpholine-3-thione

Product 1

HCID 67609461HCID 67609461, compound

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

(R)-5-(3-Bromo-5-nitro-phenyl)-5-methyl-morpholine-3-thione (2.86 g, 7.77 mmol) was dissolved in 7M NH3 in methanol (50 ml). Tert-Butylhydroperoxide (9.41 ml, 78 mmol) and ammonia hydroxide (25% sol., 21.2 ml, 136 mmol) were added and the reaction was stirred at r.t. for 2 hrs. Upon completion, 50 ml half-saturated Na2S2O3 solution was added to the reaction and the product was extracted with ethyl acetate. The organic phases were washed with water and brine, combined and dried over Na2SO4. Volatiles were removed under reduced pressure, yielding the title compound as yellowish solid. 1H-NMR (360 MHz, DMSO-d6): 8.34 (s, 1H), 8.25 (s, 1H), 8.12 (s, 1H), 5.85 (br, 2H), 4.01 (m, 1H), 3.80 (m, 1H), 3.55 (m, 1H), 1.38 (s, 3H); MS: 314 [(M+H)+].

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic phases were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. customVolatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-f5c107543764477998a5419dcec61983
Source dataset
uspto-grants-2012_12
Patent number
US08338413B1

Reaction notes

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