Ammonium Hydroxide → (1-Carbamoylmethyl)acrylic acid

HRID 1384088

Reaktionsgleichung

Reaktionsgleichung von HRID 1384088
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH2:4][C:2]1=[CH2:3].[OH-].[NH4+:10]>O1CCCC1>[C:5]([CH2:4][C:2](=[CH2:3])[C:1]([OH:7])=[O:8])(=[O:6])[NH2:10]

Komponenten

4

Edukt 2

HCID 14923Ammonium HydroxideHCID 75110Itaconic Anhydride

Produkt 1

HCID 418291(1-Carbamoylmethyl)acrylic acidAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 3 g (0.027 mol) of itaconic anhydride in 30 ml of tetrahydrofuran, 3 ml of 28% ammonium hydroxide was added. After 1 hr. the reaction mixture was evaporated to dryness under reduced pressure. The residue was dissolved in 15 ml of water, then acidified to pH 2 with concentrated hydrochloric acid and allowed to stay overnight at 4°. The precipitate formed was filtered off, washed with a small portion of cold water and dried to give 1.4 g (40% yield) of the title compound melting at 153-154° C.; NMR (DMSO-d6): 3.11 (s, 2H, CH2); 5.67,6.13 (s, s, 1H, 1H, CH); 6.7, 7.9 (broad s, s 1H, 1H, NH); 12.15 (broad s, 1H, OH).

Aufarbeitung

  1. additionwas added
  2. customthe reaction mixture was evaporated to dryness under reduced pressure
  3. dissolutionThe residue was dissolved in 15 ml of water
  4. waitto stay overnight at 4°
  5. customThe precipitate formed
  6. filtrationwas filtered off
  7. washwashed with a small portion of cold water
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5d3bc469e9704121a6420a33682afa7c
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06258806B1

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