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Anthranilic Acid → HCID 69747102, Verbindung

HRID 1061860
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1061860
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].C(=O)([O-])[O-].[Na+].[Na+].[C:17]1(C)[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.[CH4:28].Cl>O>[C:19]1([CH3:28])[C:20]([S:23]([C:6]2[CH:5]=[C:3]([NH2:4])[C:2](=[CH:8][CH:7]=2)[C:1]([OH:10])=[O:9])(=[O:24])=[O:25])=[CH:21][CH:22]=[CH:17][CH:18]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 227Anthranilic AcidHCID 297MethaneHCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 10340Sodium Carbonate

Produkt 1

HCID 69747102HCID 69747102, VerbindungAusbeute 110,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

13.7 g (0.1 mol) of anthranilic acid was added in three portions to the warmed solution of 26.0 g of sodium carbonate in 150 ml of water, 23.0 g (0.12 mol) of p-toluenesulfonyl chloride was added to the solution in 5 portions over a period of 20 minutes. Maintained the reaction mixture at 60-70° C. for additional 0.5 h, and rised to 85° C., 1.0 g of Norit was added cautiously and the solution was fitered. The filtrate was cooled and acidified with dilute HCl, the product was isolated by filtration and washed with dilute hydrochloric acid and then water. After recrystallized from 95% ethanol there was obtained the title compound (20.0 g) as white crystal, yield 68.7%, m.p. 229-232° C.

Aufarbeitung

  1. additionwas added to the solution in 5 portions over a period of 20 minutes
  2. customrised to 85° C.
  3. temperatureThe filtrate was cooled
  4. customthe product was isolated by filtration
  5. washwashed with dilute hydrochloric acid
  6. customAfter recrystallized from 95% ethanol

Quellen und Nachweise

ORD-Eintrag
ord-305f34d0431c41d5b6a1bacfb22171b7
Quelldatensatz
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06960611B2

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