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

HRID 564903

반응식

HRID 564903 반응식
[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]

참가 물질

5

반응물 3

HCID 67184N-bromobutanimide2회HCID 858672,2'-Azobis(2,4-dimethyl-4-methoxyvaleronitrile)HCID 221130132,6-dichloro-3-[N-(phthalimidoacetyl)-N-methylamino]toluene

생성물 1

HCID 221133383-bromomethyl-2,4-dichloro-N-methyl-N-(phthalimidoacetyl)aniline수율 27.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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-(phthalimido-acetyl)aniline (102 mg) as crystals.

후처리

  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

출처 및 근거

ORD 기록
ord-46456d136e9f4ba28f92bd423bcbcfdd
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06169095A

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