Acetic Acid → HCID 178503129, compound

HRID 993316Notes

Reaction equation

HRID 993316 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:14]([C:16]2[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][CH:17]=2)=O)[C:9](OCC)=[O:10])=[CH:4][CH:3]=1.O.[NH2:25][NH2:26].C(O)(=O)C.O>O1CCOCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([OH:10])=[N:25][NH:26][C:14]=2[C:16]2[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][CH:17]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 11256029Ethyl 2-(4-fluorophenyl)-3-(4-(methylthio)phenyl)-3-oxopropanoate

Product 1

HCID 178503129HCID 178503129, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of ethyl 2-(4-fluorophenyl)-3-(4-(methylthio)phenyl)-3-oxopropanoate(1.33 g, 4 mmol), prepared according to the method of Example 1A(ii), hydrazine hydrate (0.25 mL, 4.2 mmol), and acetic acid (0.25 mL, 4.2 mmol) in dioxane (50 mL), and water (5 mL) was refluxed for 24 hours and then concentrated in vacuo. Water was added to the residue, and the solid was filtered and dried in vacuo to provide the desired product (yield: 1.15 g; 95%). MS (DCI-NH3) m/z 301 (M+H)+, 318 (M+NH4)+; 1H NMR (300 MHz, DMSO-d6) δ2.47 (s, 3H), 7.12 (t, J=9 Hz, 2H), 7.26 (m, 6H).

Workup

  1. customprepared
  2. temperaturewas refluxed for 24 hours
  3. concentrationconcentrated in vacuo
  4. additionWater was added to the residue
  5. filtrationthe solid was filtered
  6. customdried in vacuo

Sources & evidence

ORD record
ord-3d78f68aff6c42d6b645a2a4eae89392
Source dataset
uspto-grants-2002_10
Patent number
US06472416B1

Reaction notes

Loading…