Sodium Acetate → HCID 11443036, compound

HRID 273175Notes

Reaction equation

HRID 273175 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11](/[CH:22]=[C:23](\[C:27]3[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=3)/[C:24]([OH:26])=[O:25])[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].CC([O-])=O.[Na+]>CCO>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([CH2:22][CH:23]([C:27]3[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=3)[C:24]([OH:26])=[O:25])[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 11167512HCID 11167512, compound

Product 1

HCID 11443036HCID 11443036, compoundYield 24.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of (E)-3-[4-(3,4-dichloro-phenyl)-5-(4-methoxy-phenyl)-1H-imidazol-2-yl]-2-m-tolyl-acrylic acid (Example 17; 50 mg, 0.084 mmol), p-toluenesulfonylhydrazide (0.24 g, 1.26 mmol) and NaOAc (0.10 g, 1.26 mmol) in EtOH (1.0 mL) was heated to 85° C. for 16 h. The reaction mixture was cooled and then purified directly by reversed-chromatography (Method B) to afford the title compound (10 mg, 20%). HPLC: Rt=1.19 (Method D). MS (ESI): mass calculated for C26H22Cl2N2O3, 480.10; m/z found, 481.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.54 (d, J=2.0 Hz, 1H), 7.44 (d, J=8.3 Hz, 1H), 7.34-7.29 (m, 2H), 7.27 (dd, J=8.3, 2.0 Hz, 1H), 7.23 (d, J=7.6 Hz, 1H), 7.17-7.10 (m, 3H), 6.96-6.91 (m, 2H), 4.40 (dd, J=10.1, 5.8 Hz, 1H), 3.86 (s, 3H), 3.61 (dd, J=14.9, 10.1 Hz, 1H), 3.29 (dd, J=14.9, 5.8 Hz, 1H), 2.34 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompurified directly by reversed-chromatography (Method B)

Sources & evidence

ORD record
ord-cdb17b1d6c2c4856a8c4a2752160d809
Source dataset
uspto-grants-2008_11
Patent number
US07456208B2

Reaction notes

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