Ammonia → HCID 178506307, compound

HRID 1822787Notes

Reaction equation

HRID 1822787 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[O:4][CH:5]=[CH:6][C:7]=1[C:8](OCC)=O.CC1C=CC(S([CH2:25][N+:26]#[C-:27])(=O)=O)=CC=1.[NH3:28]>>[F:14][C:2]([F:1])([F:13])[C:3]1[O:4][CH:5]=[CH:6][C:7]=1[C:8]1[N:28]=[CH:25][NH:26][CH:27]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 161915Tosylmethyl isocyanideHCID 4737733Ethyl 2-(trifluoromethyl)furan-3-carboxylate

Product 1

HCID 178506307HCID 178506307, compound

Procedure

Furanyl-imidazoles were prepared by the TosMIC reaction from aldehydes, which can be obtained either by reduction of acids, esters or amides; or by oxidation of primary alcohols. These procedures are well known in the literature. For example, ethyl 2-trifluoromethyl-furan-3-carboxylate (Scheme 17) prepared from literature procedures (U.S. Pat. No. 5,405,865, Apr. 11, 1995) was converted to an aldehyde by reduction of a Weinreb amide. The aldehyde was then reacted with the TosMIC and methanolic ammonia to yield 4-(2-trifluoromethyl-furan-3-yl)-imidazole.

Sources & evidence

ORD record
ord-dae82275b3864f8ebdcbb18a74860bf7
Source dataset
uspto-grants-2006_05
Patent number
US07037916B2

Reaction notes

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