Phenacyl bromide → 2-Amino-5-phenylfuran-3-carbonitrile

HRID 1891032Notes

Reaction equation

HRID 1891032 reaction equation
BrCC(C1C=CC=CC=1)=O.[NH2:11][C:12]1[O:13][C:14]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:15](C2C=CC=CC=2)[C:16]=1[C:17]#[N:18]>>[NH2:11][C:12]1[O:13][C:14]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:15][C:16]=1[C:17]#[N:18]

Participants

3

Reactant 2

HCID 6259Phenacyl bromideHCID 3896992-Amino-4,5-diphenyl-3-furonitrile

Product 1

HCID 6939612-Amino-5-phenylfuran-3-carbonitrileYield 38%

Procedure

2 was prepared in 38% yield from 2-bromo acetophenone (1), similar to 2-amino-4,5-diphenylfuran-3-carbonitrile (see Example 5 above). 1H NMR (300 MHz, CDCl3) δ 7.50-7.47 (m, 2H), 7.39-7.33 (m, 2H), 7.27-7.25 (m, 1H), 6.54 (s, 1H), 4.86 (br, 2H). LCMS (ESI) m/z 185.0 (M+H)+.

Sources & evidence

ORD record
ord-2c38911d98074961bb663487e5e39e6e
Source dataset
uspto-grants-2013_08
Patent number
US08507502B2

Reaction notes

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