Dicyclohexylcarbodiimide → 2-Amino-4-chlorobenzamide

HRID 481021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 481021
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5](=[CH:9][CH:10]=1)[C:6](O)=[O:7].C1([N:18]=C=NC2CCCCC2)CCCCC1.O.OC1C2N=NNC=2C=CC=1.[OH-].[NH4+]>CN(C)C=O>[NH2:11][C:4]1[CH:3]=[C:2]([Cl:1])[CH:10]=[CH:9][C:5]=1[C:6]([NH2:18])=[O:7]

Komponenten

6

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 14923Ammonium HydroxideHCID 666462-Amino-4-chlorobenzoic acidHCID 178526939HCID 178526939, Verbindung

Produkt 1

HCID 123748372-Amino-4-chlorobenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-chloroanthranilic acid (70 g, 0.41 mol) in hot (60° C.) dimethylformamide (700 mL), dicyclohexylcarbodiimide (93 g, 0.451 mol, 1.1 equiv), hydroxybenzotriazole hydrate (60.9 g, 0.451 mol, 1.1 eq) and 30% aqueous ammonium hydroxide solution (350 mL) were added. The resulting solution was stirred at room temperature for 18 h. The formed urea was filtered off and the filtrate concentrated. The resulting mixture was partitioned between ethyl acetate and 5% K2CO3 solution. The organic phase was separated, dried over anhydrous Na2SO4, filtered and the filtrate was concentrated to dryness to give the desired product as a slightly yellow solid (58.1 g, 83%).

Aufarbeitung

  1. filtrationThe formed urea was filtered off
  2. concentrationthe filtrate concentrated
  3. customThe resulting mixture was partitioned between ethyl acetate and 5% K2CO3 solution
  4. customThe organic phase was separated
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-910b32b685cb4b8dab9eb0804869f0b6
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06653475B2

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