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

HRID 726275

Reaktionsgleichung

Reaktionsgleichung von HRID 726275
[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-ec34f7feeb244b73b33a303662ef4650
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05708173

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