Acetic Acid → HCID 178457008, compound

HRID 80003

Reaction equation

HRID 80003 reaction equation
[C:1]1([N:7]2[C:11](=[O:12])[CH2:10][S:9]/[C:8]/2=[N:13]\[CH:14]([CH3:16])[CH3:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]([O-:20])(=[O:19])C.[Na+].[C:22](O)(=O)[CH3:23]>CC(=O)OCC>[O:19]1[C:1]2[CH:6]=[CH:5][C:22](/[CH:23]=[C:10]3/[C:11](=[O:12])[N:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)/[C:8](=[N:13]/[CH:14]([CH3:16])[CH3:15])/[S:9]/3)=[CH:3][C:2]=2[O:20][CH2:17]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 178457009HCID 178457009, compound

Product 1

HCID 178457008HCID 178457008, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-phenyl-2-[(Z)-isopropylimino]-thiazolidin-4-one (150 mg, 0.64 mmol), piperonat (192 mg, 1.28 mmol) and sodium acetate (105 mg, 1.28 mmol) in acetic acid (3 mL) is stirred at 110° C. for 4 h. The dark yellow to brown solution is cooled to rt, diluted with EA (75 mL), washed with sat. aq. NaHCO3, followed by water, and evaporated. The crude product is purified by crystallisation from a small amount of methanol (approx. 5 mL) to give 5-benzo[1,3]dioxol-5-ylmeth-(Z)-ylidene-2-[(Z)-isopropylimino]-3-phenyl-thiazolidin-4-one.

Workup

  1. washwashed with sat. aq. NaHCO3
  2. customevaporated
  3. customThe crude product is purified by crystallisation from a small amount of methanol (approx. 5 mL)

Sources & evidence

ORD record
ord-5d84672327704de68b2ec07c7ee9aeb1
Source dataset
uspto-grants-2014_09
Patent number
USRE045174E1

Linked notes

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