4-Methylmorpholine → 2-(2-nitro-1H-imidazol-1-yl)-N-(2,3,3-trifluoroallyl)-acetamide

HRID 2113915Notes

Reaction equation

HRID 2113915 reaction equation
C[N:2]1CCOCC1.[N+:8]([C:11]1[N:12]([CH2:16][C:17]([OH:19])=O)[CH:13]=[CH:14][N:15]=1)([O-:10])=[O:9].ClC(OCC(C)C)=O.Cl.[F:29][C:30](N)([F:34])[C:31]([F:33])=[CH2:32]>C1COCC1>[N+:8]([C:11]1[N:12]([CH2:16][C:17]([NH:2][CH2:32][C:31]([F:33])=[C:30]([F:34])[F:29])=[O:19])[CH:13]=[CH:14][N:15]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 3275442-(2-Nitroimidazol-1-yl)acetic acidHCID 866064551,1,2-Trifluoro allyl amine hydrochloride

Product 1

HCID 99033802-(2-nitro-1H-imidazol-1-yl)-N-(2,3,3-trifluoroallyl)-acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-methylmorpholine (1.01 g, 10 mmol) was added to 2-(2-nitro-1H-imidazol-1-yl)acetic acid (1.71 g, 10 mmol) in 150 mL of a dry THF under nitrogen at 0° C. and stirred for 10 minutes. Isobutyl chloroformate (1.43 mL, 11 mmol) was added. After 30 minutes, 1,1,2-Trifluoro allyl amine hydrochloride (1.62 g, 11 mmol) and N-methylmorpholine (1.21 g, 12 mmol) was added to the solution and the mixture stirred at room temperature overnight. The solution was then filtered and the organic solvent evaporated to give a pale yellow solid.

Workup

  1. waitAfter 30 minutes
  2. stirringthe mixture stirred at room temperature overnight
  3. filtrationThe solution was then filtered
  4. customthe organic solvent evaporated
  5. customto give a pale yellow solid

Sources & evidence

ORD record
ord-f0466fbc9cb44c2894063e2bf57e053f
Source dataset
uspto-grants-2008_10
Patent number
US07432295B2

Reaction notes

Loading…