Acetic Acid → 5447-37-0

HRID 1012211Notes

Reaction equation

HRID 1012211 reaction equation
[S:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[S:3].O=[CH:9][C:10]1[CH:18]=[CH:17][C:15]([OH:16])=[C:12]([O:13][CH3:14])[CH:11]=1.CC([O-])=O.[Na+].C(O)(=O)C>O>[OH:16][C:15]1[CH:17]=[CH:18][C:10]([CH:9]=[C:7]2[S:1][C:2](=[S:3])[NH:4][C:5]2=[O:6])=[CH:11][C:12]=1[O:13][CH3:14]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1183VanillinHCID 517045Sodium AcetateHCID 1201546Rhodanine

Product 1

HCID 28316035447-37-0Yield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a N2-purged flask was added rhodanine (574 mg, 4.31 mmol), vanillin (656 mg, 1 equiv), NaOAc (354 mg, 3.5 equiv) and acetic acid (8.5 mL). The mixture was heated at 90° C. under N2 for 20 h to yield a yellow precipitate. The reaction solution was diluted with water (150 mL) and the solid precipitate was filtered through a Buchner funnel. The solid product was washed with water, and then with hexane, then dried under high vacuum to yield the intermediate compound (770 mg, 67% yield).

Workup

  1. customTo a N2-purged flask
  2. customto yield a yellow precipitate
  3. filtrationthe solid precipitate was filtered through a Buchner funnel
  4. washThe solid product was washed with water
  5. dry with materialwith hexane, then dried under high vacuum

Sources & evidence

ORD record
ord-71cf9c0542e54c8e9f9ef6ba12a2997f
Source dataset
uspto-grants-2011_07
Patent number
US07977489B2

Reaction notes

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