Hexamethylenetetramine → 1-Amino-3-(3,4-dichlorophenyl)-3-methylbutan-2-one hydrobromide

HRID 83853Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 83853
[Br:1][CH2:2][C:3](=[O:15])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=1)([CH3:6])[CH3:5].C1N2CN3CN(C2)C[N:17]1C3>C(Cl)Cl>[BrH:1].[NH2:17][CH2:2][C:3](=[O:15])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=1)([CH3:6])[CH3:5]

Komponenten

4

Edukt 2

HCID 4101HexamethylenetetramineHCID 212583981-Bromo-3-(3,4-dichlorophenyl)-3-methylbutan-2-one

Produkt 1

HCID 667410091-Amino-3-(3,4-dichlorophenyl)-3-methylbutan-2-one hydrobromideAusbeute 158,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 1-bromo-3-(3,4-dichlorophenyl)-3-methylbutan-2-one (4.0 g, 13 mmol) and HMTA (hexamethylenetetramine, 2.0 g, 14 mmol) in DCM (25 mL) was stirred 48 h at room temperature. The volatiles were evaporated in vacuo. The crude material was dissolved in EtOH (80 mL) and combined with conc HCl (40 mL). The resulting mixture was heated at reflux 2 h, cooled to room temperature, and concentrated in vacuo to give 1-amino-3-(3,4-dichlorophenyl)-3-methylbutan-2-one hydrobromide (6.75 g), which was used in the next reaction without purification. 1H NMR (400 MHz, DMSO-d6) δ 8.00 (bs, 3H), 7.61 (d, 1H), 7.52 (d, 1H), 7.29 (dd, 1H), 3.94 (m, 2H), 1.47 (s, 6H).

Aufarbeitung

  1. customThe volatiles were evaporated in vacuo
  2. dissolutionThe crude material was dissolved in EtOH (80 mL)
  3. temperatureThe resulting mixture was heated
  4. temperatureat reflux 2 h
  5. temperaturecooled to room temperature
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-608e79795a264ebd832ad3810ac0fb79
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846739B2

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