Hydrochloric Acid → 4-(1,3-diethyl-2,3,6,7-tetrahydro-2,6-dioxo-1H-purin-8-yl)benzenesulfonic acid

HRID 1262519

Reaktionsgleichung

Reaktionsgleichung von HRID 1262519
[NH2:1][C:2]1[C:3](=[O:14])[N:4]([CH2:12][CH3:13])[C:5](=[O:11])[N:6]([CH2:9][CH3:10])[C:7]=1[NH2:8].[K+].[S:16]([C:20]1[CH:28]=[CH:27][C:23]([C:24]([O-])=O)=[CH:22][CH:21]=1)([OH:19])(=[O:18])=[O:17].C(N=C=NCCCN(C)C)C.Cl>O>[CH2:12]([N:4]1[C:3](=[O:14])[C:2]2[NH:1][C:24]([C:23]3[CH:22]=[CH:21][C:20]([S:16]([OH:19])(=[O:18])=[O:17])=[CH:28][CH:27]=3)=[N:8][C:7]=2[N:6]([CH2:9][CH3:10])[C:5]1=[O:11])[CH3:13]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 45721335,6-Diamino-1,3-diethyluracilHCID 23670833Potassium 4-carboxybenzenesulfonate

Produkt 1

HCID 155873004-(1,3-diethyl-2,3,6,7-tetrahydro-2,6-dioxo-1H-purin-8-yl)benzenesulfonic acidAusbeute 67,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 5,6-diamino-1,3-diethyl-2,4(1H,3H)-pyrimidinedione (41.2 g, 0.208 moles), 4-sulfobenzoic acid monopotassium salt (50.0 g, 0.208 moles), and water (250 ml) is prepared, and the pH adjusted to 6.0. Ethyl-3-(3-dimethylaminopropyl)carbodiimide (39.9 g, 0.208 moles) is added in one portion, and the pH of the resulting solution maintained at 5.5±0.5 with the dropwise addition of 4 N hydrochloric acid. When the pH of the solution ceases to rise, the mixture is concentrated on a rotary evaporator, and the residue taken up in 400 ml 10% potassium hydroxide and stirred for 18 hours. At the end of this time, the solution is boiled under reflux for one hour, cooled, filtered, and made acidic with the portionwise addition of 12 N hydrochloric acid. The resulting suspension is cooled and filtered; the solids are triturated with ethanol, filtered, and dried to yield 51.2 grams of 4-(1,3-diethyl-2,3,6,7-tetrahydro-2,6-dioxo-1H-purin-8-yl)-benzenesulfonic acid; mp greater than 360° C.

Aufarbeitung

  1. customis prepared
  2. concentrationthe mixture is concentrated on a rotary evaporator
  3. temperatureunder reflux for one hour
  4. temperaturecooled
  5. filtrationfiltered
  6. additionmade acidic with the portionwise addition of 12 N hydrochloric acid
  7. temperatureThe resulting suspension is cooled
  8. filtrationfiltered
  9. customthe solids are triturated with ethanol
  10. filtrationfiltered
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-081a38aa30294bcbab0cad4c11d72b5b
Quelldatensatz
uspto-grants-1984_06
Patentnummer
US04452788

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