Potassium Carbonate → N-(1-isopropylpyrazol-5-yl)-5-(diethylaminosulfonyl) anthranilic acid

HRID 375898Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 375898
[NH2:1][C:2]1[N:6]([CH:7]([CH3:9])[CH3:8])[N:5]=[CH:4][CH:3]=1.Cl[C:11]1[CH:19]=[CH:18][C:17]([S:20]([N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])(=[O:22])=[O:21])=[CH:16][C:12]=1[C:13]([OH:15])=[O:14].C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Cu+2].CN(C=O)C>[CH:7]([N:6]1[C:2]([NH:1][C:11]2[C:12](=[CH:16][C:17]([S:20]([N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])(=[O:21])=[O:22])=[CH:18][CH:19]=2)[C:13]([OH:15])=[O:14])=[CH:3][CH:4]=[N:5]1)([CH3:9])[CH3:8]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 7678952-Chloro-5-(diethylsulfamoyl)benzoic acidHCID 10903411-(propan-2-yl)-1H-pyrazol-5-amine

Produkt 1

HCID 54426707N-(1-isopropylpyrazol-5-yl)-5-(diethylaminosulfonyl) anthranilic acidAusbeute 62,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 5-amino-1-isopropylpyrazole (6.43 g, 0.051 mol), 2-chloro-5-(diethylaminosulfonyl)benzoic acid (15.0 g, 0.051 mol), K2CO3 (7.04 g, 0.051 mol), Cu(OAc)2 (1.0 g) and DMF (100 mL) was refluxed for 24 hours. The reaction mixture was concentrated in vacuo and the residue was poured into water and neutralized with acetic acid. The mixture was extracted with CH2Cl2 and the CH2Cl2 layer was dried over MgSO4 and evaporated to afford 12.1 g of N-(1-isopropylpyrazol-5-yl)-5-(diethylaminosulfonyl) anthranilic acid.

Aufarbeitung

  1. temperaturewas refluxed for 24 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionthe residue was poured into water and neutralized with acetic acid
  4. extractionThe mixture was extracted with CH2Cl2
  5. dry with materialthe CH2Cl2 layer was dried over MgSO4
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-7a29c6d369524198a1e96d492f38183b
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05488055

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