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Triethylamine → N-(2,2,2-trifluoro)ethyl-2-(4-nitro-1H-imidazol-1-yl)octanoamide

HRID 375115
Notes
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Reaction equation

HRID 375115 reaction equation
[N+:1]([C:4]1[N:5]=[CH:6][N:7]([CH:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:10]([OH:12])=O)[CH:8]=1)([O-:3])=[O:2].C(Cl)(=O)C(Cl)=O.Cl.[F:26][C:27]([F:31])([F:30])[CH2:28][NH2:29].C(N(CC)CC)C>C1COCC1>[F:26][C:27]([F:31])([F:30])[CH2:28][NH:29][C:10](=[O:12])[CH:9]([N:7]1[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[N:5]=[CH:6]1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 97722,2,2-Trifluoroethylamine hydrochlorideHCID 65578Oxalyl chlorideHCID 100836862-(4-nitro-1H-imidazol-1-yl)octanoic acid

Product 1

HCID 15222341N-(2,2,2-trifluoro)ethyl-2-(4-nitro-1H-imidazol-1-yl)octanoamideYield 22.9%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

2-(4-Nitro-1H-imidazol-1-yl)octanoic acid (7.8 mmoles,2.0 g) was treated with 25 ml oxalyl chloride, concentrated and added to a solution of trifluoroethylamine hydrochloride (7.8 mmoles, 1.06 g) and triethylamine (2 ml) in 50 ml THF. After stirring at room temperature for 16 hours, the mixture was added to ice, extracted with ethyl acetate, dried over sodium sulfate, and concentrated. The intermediate was chromatographed over silica gel to yield 0.6 g of N-(2,2,2-trifluoro)ethyl-2-(4-nitro-1H-imidazol-1-yl)octanoamide. (MS).

Workup

  1. concentrationconcentrated
  2. additionthe mixture was added to ice
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe intermediate was chromatographed over silica gel

Sources & evidence

ORD record
ord-233f3d3d294447f88067464e0e95f6fb
Source dataset
uspto-grants-1996_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05484780

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes