Acetic Acid → Methyl 5-(2,4-dioxothiazolidin-5-ylidene)methyl-2-methoxybenzoate

HRID 378341

Reaktionsgleichung

Reaktionsgleichung von HRID 378341
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:13][CH3:14])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])=O.[S:15]1[CH2:19][C:18](=[O:20])[NH:17][C:16]1=[O:21].C([O-])(=O)C.[NH4+].C(O)(=O)C>C1C=CC=CC=1>[O:21]=[C:16]1[NH:17][C:18](=[O:20])[C:19](=[CH:1][C:3]2[CH:4]=[CH:5][C:6]([O:13][CH3:14])=[C:7]([CH:12]=2)[C:8]([O:10][CH3:11])=[O:9])[S:15]1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 5437ThiazolidinedioneHCID 517165Ammonium AcetateHCID 10856352Methyl 5-formyl-2-methoxybenzoate

Produkt 1

HCID 54363563Methyl 5-(2,4-dioxothiazolidin-5-ylidene)methyl-2-methoxybenzoateAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A mixture of methyl 5-formyl-2-methoxybenzoate (490 mg), thiazolidine-2,4-dione (358 mg), ammonium acetate (401 mg), acetic acid (0.8 ml) and benzene (10 ml) was submitted to Dean-Stalk dewatering apparatus to reflux for 4 hours under heat. After cooling, the crystals deposited were collected by filtration, washed with benzene and with 20% aqueous solution of acetone, and then dried to obtain 634 mg (86%) of aimed compound as crystals.

Aufarbeitung

  1. temperatureto reflux for 4 hours
  2. temperatureunder heat
  3. temperatureAfter cooling
  4. filtrationthe crystals deposited were collected by filtration
  5. washwashed with benzene and with 20% aqueous solution of acetone
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-03287fb8b777420db9a2b3b5043438ca
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06030990

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