Diethylamine → 4-benzoyl-N,N-diethylbenzamide

HRID 1267501

Reaktionsgleichung

Reaktionsgleichung von HRID 1267501
[C:1]([C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=S(Cl)Cl.[CH2:22]([NH:24][CH2:25][CH3:26])[CH3:23]>[OH-].[Na+].C(Cl)Cl>[CH2:22]([N:24]([CH2:25][CH3:26])[C:13](=[O:15])[C:12]1[CH:11]=[CH:10][C:9]([C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:17][CH:16]=1)[CH3:23]

Komponenten

6

Edukt 3

HCID 8021DiethylamineHCID 24386Thionyl ChlorideHCID 691474-Benzoylbenzoic acid

Produkt 1

HCID 7559904-benzoyl-N,N-diethylbenzamideAusbeute 95,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A solution of 25 g (110 mmol) 4-benzoylbenzoic acid [611-95-0] and 20 mL SOCl2 was allowed to reflux for 2 h then allowed to cool. The excess SOCl2 was evaporated off and the resulting clear oil was dissolved in 10 mL CH2Cl2 then slowly added to 12 mL (116 mmol) diethylamine in a mixture of 10 mL 3N NaOH and 50 mL CH2Cl2. The mixture was allowed to stir for 30 min then partitioned between H2O and CH2Cl2. The organic layer was washed with brine, dried over K2CO3, filtered and concentrated. The product precipitated from EtOAc/hexane to give 29.6 g (105 mmol) white crystals. MS m/z (MH+) 282.

Aufarbeitung

  1. temperatureto reflux for 2 h
  2. temperatureto cool
  3. customThe excess SOCl2 was evaporated off
  4. dissolutionthe resulting clear oil was dissolved in 10 mL CH2Cl2
  5. customthen partitioned between H2O and CH2Cl2
  6. washThe organic layer was washed with brine
  7. dry with materialdried over K2CO3
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe product precipitated from EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-b6906a990c194f889bb665cdfe1b54fa
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06552036B2

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