1,1,1-Trifluoro-2-iodoethane → HCID 24965850, compound

HRID 1092322Notes

Reaction equation

HRID 1092322 reaction equation
[CH2:1]([C:5]1[NH:6][C:7](=[O:20])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:19])([F:18])[F:17])[CH:9]=1)[CH:2]([CH3:4])[CH3:3].[F:21][C:22]([F:26])([F:25])[CH2:23]I.N1C(=O)N=CC=1>>[CH2:1]([C:5]1[NH:6][C:7](=[O:20])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:19])([F:17])[F:18])[C:9]=1[CH2:23][C:22]([F:26])([F:25])[F:21])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 3

HCID 677091,1,1-Trifluoro-2-iodoethaneHCID 118190392H-Imidazol-2-oneHCID 24964795HCID 24964795, compound

Product 1

HCID 24965850HCID 24965850, compoundYield 14%

Procedure

This material was obtained in analogy to the procedure outlined in example 23 from 4-isobutyl-1-(2-trifluoromethyl-phenyl)-1,3-dihydro-imidazol-2-one (obtained in example 18, 200 mg) by alkylation with 2,2,2-trifluoroethyl iodide (162 mg). In contrast to the other, similar reactions, alkylation occurred predominantly at C-5 instead of N-3 of the imidazolone core. Thus, this reaction yielded 4-isobutyl-5-(2,2,2-trifluoro-ethyl)-1-(2-trifluoromethyl-phenyl)-1,3-dihydro-imidazol-2-one as a light yellow solid (36 mg). MS (ESI): 367.0 (MH+).

Workup

  1. customThis material was obtained in analogy to the procedure

Sources & evidence

ORD record
ord-c05f0ea679d449758d12f6949355b823
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

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