Sodium Iodide → 5-chloro-2-{[N-(diphenylmethyl)glycyl]amino}benzoic acid

HRID 1626759

Reaktionsgleichung

Reaktionsgleichung von HRID 1626759
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][C:12](=[O:15])[CH2:13]Cl)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH:16]([NH2:29])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[I-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][C:12](=[O:15])[CH2:13][NH:29][CH:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Komponenten

6

Edukt 3

HCID 5238Sodium IodideHCID 7036BenzhydrylamineHCID 41798255-Chloro-2-((2-chloroacetyl)amino)benzoic acid

Produkt 1

HCID 666802955-chloro-2-{[N-(diphenylmethyl)glycyl]amino}benzoic acidAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1.0 g (4.0 mmol) of 5-chloro-2-[(chloroacetyl)amino]benzoic acid obtained in Example 72-(i), 2.94 g (16.0 mmol) of benzhydrylamine, and 60 mg (0.4 mmol) of sodium iodide were stirred in 3 mL of DMF solution at 80° C. for 1 hour. Thereafter, the mixture was diluted with ethyl acetate, and washed with 1N hydrochloric acid. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. Ethyl acetate was added to the condensed residue, and solids were collected by filtration, followed by drying, thereby giving 744 mg of the target 5-chloro-2-{[N-(diphenylmethyl)glycyl]amino}benzoic acid (yield: 49%).

Aufarbeitung

  1. washwashed with 1N hydrochloric acid
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionEthyl acetate was added to the condensed residue, and solids
  5. filtrationwere collected by filtration
  6. customby drying

Quellen und Nachweise

ORD-Eintrag
ord-3d7be04a68e4440b9598f4d2a2b67d72
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785473B2

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