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Triethylamine → N-[2,6-dibromo-4-(1,2,2,3,3,3-hexafluoro-1-trifluoromethylpropyl)phenyl]-3-nitro-4-(1,2,4-triazol-1-yl)benzamide

HRID 1253404
Notes
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Reaction equation

HRID 1253404 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:20])([C:16]([F:19])([F:18])[F:17])[C:9]([F:15])([F:14])[C:10]([F:13])([F:12])[F:11])[CH:5]=[C:4]([Br:21])[C:3]=1[NH2:22].C(N(CC)CC)C.[N+:30]([C:33]1[CH:34]=[C:35]([CH:39]=[CH:40][C:41]=1[N:42]1[CH:46]=[N:45][CH:44]=[N:43]1)[C:36](O)=[O:37])([O-:32])=[O:31].O=C1N([ClH]P([ClH]N2CCOC2=O)=O)CCO1>ClCCCl>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:20])([C:16]([F:17])([F:18])[F:19])[C:9]([F:14])([F:15])[C:10]([F:11])([F:13])[F:12])[CH:5]=[C:4]([Br:21])[C:3]=1[NH:22][C:36](=[O:37])[C:35]1[CH:39]=[CH:40][C:41]([N:42]2[CH:46]=[N:45][CH:44]=[N:43]2)=[C:33]([N+:30]([O-:32])=[O:31])[CH:34]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 20600963-Nitro-4-(1H-1,2,4-triazol-1-yl)benzoic acid2×HCID 582974122,6-Dibromo-4-(perfluorobutan-2-yl)aniline

Product 1

HCID 46944258N-[2,6-dibromo-4-(1,2,2,3,3,3-hexafluoro-1-trifluoromethylpropyl)phenyl]-3-nitro-4-(1,2,4-triazol-1-yl)benzamideYield 65%

Reagents, catalysts & solvents 1

HCID 11
1,2-Dichloroethane
Solvent

Procedure

To a suspension of 2,6-dibromo-4-(1,2,2,3,3,3-hexafluoro-1-trifluoromethylpropyl)-phenylamine (Example I1) (635 mg, 1.35 mmol) in 1,2-dichloroethane (6.5 ml) was added triethylamine (0.57 ml, 4.06 mmol), followed by 3-nitro-4-(1H-1,2,4-triazol-1-yl)benzoic acid (634 mg, 2.7 mmol) and bis(2-oxo-3-oxazolidinyl)phosphonic chloride (“BOP—Cl”) (689 mg, 2.7 mmol). The reaction mixture was stirred at reflux for 16 hours. The progress of the reaction was followed by thin layer chromatography and, because it was necessary in this case, further doses of 3-nitro-4-(1H-1,2,4-triazol-1-yl)benzoic acid (4×0.675 mmol), bis(2-oxo-3-oxazolidinyl)phosphonic chloride (4×1.35 mmol) and triethylamine (4×1.35 mmol) were added over the course of 48 hours. The reaction was quenched by addition of aqueous hydrochloric acid (1M) and the phases were separated. The organic phase was washed with saturated aqueous sodium hydrogen carbonate, dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:2) to give Compound No. A4 of Table A (605 mg, 65% yield).

Workup

  1. temperatureat reflux for 16 hours
  2. additionwere added over the course of 48 hours
  3. customThe reaction was quenched by addition of aqueous hydrochloric acid (1M)
  4. customthe phases were separated
  5. washThe organic phase was washed with saturated aqueous sodium hydrogen carbonate
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:2)
  9. customto give Compound No

Sources & evidence

ORD record
ord-71cd7e5225e74cba9a6f3a9e4173b2dd
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08455399B2

Reaction notes

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