3-Chlorobenzoic Acid → N-(3-butyramidophenyl)-3-chlorobenzamide

HRID 1484537Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1484537
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:13])[CH2:10][CH2:11][CH3:12])[CH:5]=[CH:6][CH:7]=1.[Cl:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18](O)=[O:19].C1C=CC2N(O)N=NC=2C=1.C(Cl)Cl>CC#N.C(Cl)Cl>[C:9]([NH:8][C:4]1[CH:3]=[C:2]([NH:1][C:18](=[O:19])[C:17]2[CH:21]=[CH:22][CH:23]=[C:15]([Cl:14])[CH:16]=2)[CH:7]=[CH:6][CH:5]=1)(=[O:13])[CH2:10][CH2:11][CH3:12]

Komponenten

6

Edukt 4

HCID 4473-Chlorobenzoic AcidHCID 6344DichloromethaneHCID 757711-HydroxybenzotriazoleHCID 721132N-(3-aminophenyl)butanamide

Produkt 1

HCID 17187580N-(3-butyramidophenyl)-3-chlorobenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21877088Acetonitrile methylene chlorideLösungsmittel

Versuchsvorschrift

N-(3-Aminophenyl)butyramide (30 mg, 0.168 mmol), 3-chlorobenzoic acid (39.5 mg, 0.252 mmol), HOBt (28.4 mg, 0.185 mmol), and silica-supported DCC (from Silicycle Inc., 362 mg, 0.337 mmol) were added to a 13×100 mm test tube with stir bar. The tube was sealed with a rubber septum and dry DCM (3 mL) was added, then the reaction was stirred for 15 h. 50% CH3CN/DCM (4 mL) was then added, followed by silica-supported trimethylammonium carbonate (from Silicycle Inc., 534 mg, 0.337 mmol). The mixture was stirred for 1 h, then filtered through Celite and washed with 50% CH3CN/DCM (4 mL) and concentrated. The crude solid was redissolved with DCM and purified by column chromatography (EtOAc/hexanes gradient) to yield a white solid after precipitating from hexanes (39 mg, 73%). LRMS (ESI+) (M+H): 317.22.

Aufarbeitung

  1. additionwas added
  2. stirringthe reaction was stirred for 15 h
  3. stirringThe mixture was stirred for 1 h
  4. filtrationfiltered through Celite
  5. washwashed with 50% CH3CN/DCM (4 mL)
  6. concentrationconcentrated
  7. dissolutionThe crude solid was redissolved with DCM
  8. custompurified by column chromatography (EtOAc/hexanes gradient)
  9. customto yield a white solid
  10. customafter precipitating from hexanes (39 mg, 73%)

Quellen und Nachweise

ORD-Eintrag
ord-0dab99644fdd47739773ae3bbd708321
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09422262B2

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