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

HRID 581747

反応式

HRID 581747 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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. mp: 211° C. (dec.)

後処理

  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

出典と根拠

ORDレコード
ord-0dea4617883b498bbc4be403d81c099a
出典データセット
uspto-grants-1999_07
特許番号
US05922711

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