4-Acetylbenzoic Acid → 4-{3E-[2,4-Dimethoxy-5-(2H-tetrazol-5-yl)-phenyl]-acryloyl}-benzoic acid

HRID 10697Notes

Reaction equation

HRID 10697 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([C:13]2[N:14]=[N:15][NH:16][N:17]=2)=[CH:7][C:4]=1[CH:5]=O.[C:18]([C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1)(=[O:20])[CH3:19]>CC#N>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([C:13]2[N:14]=[N:15][NH:16][N:17]=2)=[CH:7][C:4]=1/[CH:5]=[CH:19]/[C:18]([C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1)=[O:20]

Participants

4

Reactant 2

HCID 114704-Acetylbenzoic AcidHCID 219810812,4-dimethoxy-5-(2H-tetrazol-5-yl)-benzaldehyde

Product 1

HCID 101264304-{3E-[2,4-Dimethoxy-5-(2H-tetrazol-5-yl)-phenyl]-acryloyl}-benzoic acidYield 19%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared by condensing 2,4-dimethoxy-5-(2H-tetrazol-5-yl)-benzaldehyde (Ex-75A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, 19% yield, mp 218° C. (dec). 1H-NMR (DMSO-d6) δ 8.58 (s, 1H), 8.20 (d, 2H), 8.03 (m, 3H), 7.85 (d, 1H), 6.90 (s, 1H), 4.04 (s, 3H), 4.02 (s, 3H). MS m/z=422 ([M+CH3CN+H]+, 100%). HRMS m/z: calc. 381.1199, found 381.1184.

Sources & evidence

ORD record
ord-1a106097291b4be188bdf9f422a00973
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Reaction notes

Loading…