Triethylamine → HCID 21069869, compound

HRID 348136Notes

Reaction equation

HRID 348136 reaction equation
[C:1]1([CH3:14])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2([C:10]([F:13])([F:12])[F:11])[NH:9][NH:8]2)[CH:2]=1.C(N(CC)CC)C.ClOC(C)(C)C.S([O-])([O-])=O.[Na+].[Na+]>C(O)C>[C:1]1([CH3:14])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2([C:10]([F:11])([F:13])[F:12])[N:9]=[N:8]2)[CH:2]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24437Sodium SulfiteHCID 521297Tert-Butyl hypochloriteHCID 21069870HCID 21069870, compound

Product 1

HCID 21069869HCID 21069869, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a cold stirring solution of 3-m-tolyl-3-trifluoromethyl-diaziridine (2.0 g, 10 mmol. prepared using the methods described in Doucet-Personeni C. et al., J. Med. Chem., 2001, 44, 3203 and Nassal, M. Liebigs Ann. Chem. 1983, 1510–1523 or in Stromgaard, K et al., J. Med. Chem., 2002, 45, 4038–46) in ethanol (20 mL) was added triethylamine (1.5 g, 15 mmol). To this mixture was added tert-butyl hypochlorite (3.25 g, 30 mmol), and the mixture stirred for 5 min. This mixture was poured into 10% aqueous sodium sulfite (100 mL), and extracted with ether. The ether extract was washed with brine, dried (MgSO4), filtered and concentrated. The residue was purified by column chromatography (SiO2, pentane) to provide 1.6 g (Yield 80%) of the title compound. 1H NMR (300 MHz, CDCl3) δ ppm: 2.33 (3H, s) 6.90–7.03 (2H, m) 7.15–7.31 (2H, m).

Workup

  1. customprepared
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washwas washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (SiO2, pentane)

Sources & evidence

ORD record
ord-14712689017d428dbb0374f3e17491aa
Source dataset
uspto-grants-2007_02
Patent number
US07176196B2

Reaction notes

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