Acetic Anhydride → (E)-3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)-2-propenoic acid

HRID 1646123Notes

Reaction equation

[CH2:1]([C:5]1[N:6]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:7]([CH:10]=O)=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[CH2:25][C:26]([OH:28])=[O:27].C(=O)([O-])[O-].[K+].[K+].C(OC(=O)C)(=O)C>O>[CH2:1]([C:5]1[N:6]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:7](/[CH:10]=[C:25](/[C:21]2[S:20][CH:24]=[CH:23][CH:22]=2)\[C:26]([OH:28])=[O:27])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 2-n-butyl-1-(2-chlorophenyl)methyl-1H-imidazol-5-carboxaldehyde (2 mmol), 2-thienylacetic acid (2.3 mmol), potassium carbonate (0.91 mmol), and acetic anhydride (1 mL) is heated gradually to 140° C. and held at this temperature for 6 hours. The cooled reaction is diluted with water and the solid is separated, triturated several times with ether, and the solid is crystallized to give (E)-3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)-2-propenoic acid. The title tetrazole compound is prepared from this acid by the procedure described in Example 1.

Workup

customThe cooled reaction
customthe solid is separated
customtriturated several times with ether
customthe solid is crystallized

Sources & evidence

ORD record: ord-097494acebf2430ab72ebee9f52f7543
Source dataset: uspto-grants-1993_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05177096

Reaction notes

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