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

HRID 1609761Notes

Reaction equation

HRID 1609761 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]

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 8028TetrahydrofuranSolvent

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-c658491962134bf091fcb513b8906862
Source dataset
uspto-grants-1995_03
Patent number
US05401851

Reaction notes

Loading…