Dabco → HCID 69518511, compound

HRID 1831243Notes

Reaction equation

HRID 1831243 reaction equation
[OH:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([N+:12]([O-:14])=[O:13])=[CH:4][N:3]=1.[CH3:15][N:16]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:17](Cl)=[O:18].N12CCN(CC1)CC2>O1CCCC1>[N+:12]([C:5]1[CH:6]=[C:7]([C:8]([F:11])([F:9])[F:10])[C:2]([O:1][C:17](=[O:18])[N:16]([CH3:15])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:3][CH:4]=1)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 9237DabcoHCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 178526837HCID 178526837, compound

Product 1

HCID 69518511HCID 69518511, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-hydroxy-5-nitro-3-(trifluoromethyl)pyridine (0.36 g, 1.73 mmol), N-methyl-N-phenylcarbamoyl chloride (0.44 g, 2.59 mmol) and 1,4-diazabicyclo[2.2.2]octane (0.29 g, 2.59 mmol) in tetrahydrofuran (15 ml) was stirred at room temperature for 18 hours. The solvent was evaporated in vacuo and the residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane (15:85)) yielding the title compound (0.55 g, 92% yield) as an orange solid.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane (15:85))

Sources & evidence

ORD record
ord-36cb312306e14300aacf544fd4816908
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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