Azetidine → HCID 58964519, compound

HRID 2069272Notes

Reaction equation

HRID 2069272 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8](F)[C:7]([C:11]([F:14])([F:13])[F:12])=[CH:6][C:5]=1[N+:15]([O-:17])=[O:16].[NH:19]1[CH2:22][CH2:21][CH2:20]1>O1CCCC1>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([N:19]2[CH2:22][CH2:21][CH2:20]2)[C:7]([C:11]([F:14])([F:13])[F:12])=[CH:6][C:5]=1[N+:15]([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 10422AzetidineHCID 589644905-Fluoro-2-nitro-4-trifluoromethyl-benzoic acid methyl ester

Product 1

HCID 58964519HCID 58964519, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.07 g (4.0 mmol) of 5-fluoro-2-nitro-4-trifluoromethyl-benzoic acid methyl ester and 0.461 ml (6.8 mmol) of azetidine in 10 ml of tetrahydrofuran is heated at reflux for 90 minutes. After evaporation of the tetrahydrofuran the residue is distributed between water and ethyl acetate, the organic phase separated and washed with water and brine, dried over Na2SO4 and concentrated yielding 1.19 g of 5-azetidin-1-yl-2-nitro-4-trifluoromethyl-benzoic acid methyl ester as yellow powder, m.p. 127-136° C.

Workup

  1. temperatureat reflux for 90 minutes
  2. customAfter evaporation of the tetrahydrofuran the residue
  3. customthe organic phase separated
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f4df0da84b9d41faad2b0a08aa484881
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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