N-bromobutanimide → 3-bromomethyl-2,4-dichloro-N-methyl-N-(phthalimidoacetyl)aniline

HRID 864554

Reaktionsgleichung

Reaktionsgleichung von HRID 864554
[Cl:1][C:2]1[C:7]([N:8]([C:10](=[O:23])[CH2:11][N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])[CH3:9])=[CH:6][CH:5]=[C:4]([Cl:24])[C:3]=1[CH3:25].[Br:26]N1C(=O)CCC1=O.N(C(C)(CC(C)(OC)C)C#N)=NC(C)(CC(OC)(C)C)C#N>ClCCl>[Br:26][CH2:25][C:3]1[C:2]([Cl:1])=[C:7]([CH:6]=[CH:5][C:4]=1[Cl:24])[N:8]([CH3:9])[C:10](=[O:23])[CH2:11][N:12]1[C:13](=[O:22])[C:14]2=[CH:21][CH:20]=[CH:19][CH:18]=[C:15]2[C:16]1=[O:17]

Komponenten

5

Edukt 3

HCID 67184N-bromobutanimide2×HCID 858672,2'-Azobis(2,4-dimethyl-4-methoxyvaleronitrile)HCID 221130132,6-dichloro-3-[N-(phthalimidoacetyl)-N-methylamino]toluene

Produkt 1

HCID 221133383-bromomethyl-2,4-dichloro-N-methyl-N-(phthalimidoacetyl)anilineAusbeute 27,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 2,6-dichloro-3-[N-(phthalimidoacetyl)-N-methylamino]toluene (303 mg), N-bromosuccinimide (150 mg), 2,2'-azobis-(2,4-dimethyl-4-methoxyvaleronitrile) (30 mg) and dichloromethane (6 ml) was heated under reflux for 5 hours. N-Bromosuccinimide (75 mg) was added therein and the mixture was heated under reflux for additional 3 hours. The reaction mixture was washed with saturated sodium bicarbonate solution twice and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from diethyl ether to give 3-bromomethyl-2,4-dichloro-N-methyl-N-(phthalimidoacetyl)aniline (102 mg) as crystals.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for additional 3 hours
  5. washThe reaction mixture was washed with saturated sodium bicarbonate solution twice
  6. dry with materialbrine, dried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was crystallized from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-376b0ed092ba423bac95ad2b6d5e7678
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05563162

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