HCID 59857983, compound → HCID 178492962, compound

HRID 1928551Notes

Reaction equation

HRID 1928551 reaction equation
[Cl:1][C:2]1[C:3]([O:16][CH3:17])=[C:4]([NH:8][C:9](=[O:15])/[CH:10]=[CH:11]/OCC)[CH:5]=[CH:6][CH:7]=1>OS(O)(=O)=O>[Cl:1][C:2]1[C:3]([O:16][CH3:17])=[C:4]2[C:5]([CH:11]=[CH:10][C:9]([OH:15])=[N:8]2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 59857983HCID 59857983, compound

Product 1

HCID 178492962HCID 178492962, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To conc H2SO4 (30 mL) was added to (E)-N-(3-chloro-2-methoxyphenyl)-3-ethoxypropenamide (3b) (3.73 g, 14.6 mmol) and allowed to stir overnight. The solution was poured over ice, filtered, washed and dried to give a yellow solid (2.85 g, 93% yield): 1H NMR (400 MHz, DMSO-d6) 11.45 (bs, 1H), 7.89 (d, J=10 Hz, 1H), 7.44 (d, J=8.4 Hz, 1H), 7.23 (d, J=8.8 Hz, 1H), 6.52 (d, J=10 Hz, 1H), 3.81 (s, 3H).

Workup

  1. additionThe solution was poured over ice
  2. filtrationfiltered
  3. washwashed
  4. customdried

Sources & evidence

ORD record
ord-07800142cc6e4341a626c3e18a2c6303
Source dataset
uspto-grants-2012_05
Patent number
US08183379B2

Reaction notes

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