Tert-Butylamine → N-T-BUTYL-2-METHYLBENZAMIDE

HRID 400270Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 400270
[C:1]1([CH3:10])[C:2]([C:7](Cl)=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.C(N(CC)CC)C.[C:18]([NH2:22])([CH3:21])([CH3:20])[CH3:19]>C(Cl)Cl.O>[C:18]([NH:22][C:7](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH3:10])([CH3:21])([CH3:20])[CH3:19]

Komponenten

6

Edukt 3

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 702762-Methylbenzoyl chloride

Produkt 1

HCID 5071216N-T-BUTYL-2-METHYLBENZAMIDEAusbeute 97,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a cold (0° C.) solution of 139.2 g (0.9 mol) of o-toluoyl chloride in 1200 mL of methylene chloride at 25° C., under nitrogen, was slowly added 180.0 g (1.8 mol) of triethylamine followed by the dropwise addition of a solution containing 73.14 g (1.0 mol) of t-butylamine in 200 mL of methylene chloride. The resulting reaction mixture was warmed to room temperature and allowed to react for 2.5 hours. The reaction mixture was then diluted with 1800 mL of water. The resulting organic and aqueous layers were separated, and the organic layer was washed sequentially with 2N sodium hydroxide, 1.0N hydrochloric acid and brine, dried over magnesium sulfate, filtered and then reduced to dryness under reduced pressure to provide 167.6 g of the desired subtitled compound as an off-white solid (mp 77°-78° C.).

Aufarbeitung

  1. customat 25° C.
  2. additionfollowed by the dropwise addition of a solution
  3. customThe resulting reaction mixture
  4. customto react for 2.5 hours
  5. customThe resulting organic and aqueous layers were separated
  6. washthe organic layer was washed sequentially with 2N sodium hydroxide, 1.0N hydrochloric acid and brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-5196e6d6be534c39b9007841eecea447
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05827891

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