Piperonal → HCID 178457008, compound

HRID 1879502

Reaction equation

HRID 1879502 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.[CH:17]1[C:22]([CH:23]=O)=[CH:21][C:20]2[O:25][CH2:26][O:27][C:19]=2[CH:18]=1.C([O-])(=O)C.[Na+]>C(O)(=O)C.CC(=O)OCC>[O:27]1[C:19]2[CH:18]=[CH:17][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:21][C:20]=2[O:25][CH2:26]1

Participants

6

Reactant 3

HCID 8438PiperonalHCID 517045Sodium AcetateHCID 178457009HCID 178457009, compound

Product 1

HCID 178457008HCID 178457008, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-phenyl-2-[(Z)-isopropylimino]-thiazolidin-4-one (150 mg, 0.64 mmol), piperonal (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-19e755af9dc0423db1cfdc41f5f6eb39
Source dataset
uspto-grants-2012_11
Patent number
USRE043833E1

Linked notes

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