Oxalyl chloride → HCID 68538664, compound

HRID 1993575Notes

Reaction equation

HRID 1993575 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[C:7]([OH:9])=O)([O-:3])=[O:2].C(Cl)(=O)C(Cl)=O.[CH2:23]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)[CH3:24]>CN(C=O)C.C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]([C:7]([N:28]2[CH2:29][CH2:30][N:25]([CH2:23][CH3:24])[CH2:26][CH2:27]2)=[O:9])[CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 791961-EthylpiperazineHCID 6166023-Nitro-5-(trifluoromethyl)benzoic acid

Product 1

HCID 68538664HCID 68538664, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

In an ice bath under N2-atmosphere, 3-nitro-5-trifluoromethyl-benzoic acid (Lancaster; 11.8 g, 50 mmol), CH2Cl2 (150 ml), a few drops of DMF and oxalylchloride ( 7.0 ml, 81 mmol) are mixed and then stirred for 3 h at rt. The resulting solution is concentrated in vacuo. The residue is dissolved in CH2Cl2 (170 ml) and added dropwise to an ice cooled solution of N-ethyl-piperazine (12.7 ml, 0.10 mol) in CH2Cl2 (100 ml). After stirring for 1 h at rt, the mixture is washed with a diluted solution of Na2CO3, 2 portions of water and finally brine. The aqueous layers are re-extracted twice with AcOEt, the combined organic phases dried (Na2SO4) and concentrated giving the title compound as an oil: MS: [M+1]+=332; 1H-NMR (CDCl3): 8.53 (s, 1H), 8.44 (s, 1H), 8.00 (s, 1H), 3.84 (m, 2H), 3.43 (m, 2H), 2.57 (m, 2H), 2.48 (q, 2H), 2.44 (m, 2H), 1.12 (t, 3H).

Workup

  1. concentrationThe resulting solution is concentrated in vacuo
  2. dissolutionThe residue is dissolved in CH2Cl2 (170 ml)
  3. stirringAfter stirring for 1 h at rt
  4. washthe mixture is washed with a diluted solution of Na2CO3, 2 portions of water and finally brine
  5. extractionThe aqueous layers are re-extracted twice with AcOEt
  6. dry with materialthe combined organic phases dried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-52e5454aec7b48339edae69963eb6c0d
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

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