N-3-Bromopropylphthalimide → N-[3-(N-phenyl-N-pyrid-2-ylamino)propyl]phthalimide

HRID 2308984ノート

反応式

HRID 2308984 の反応式
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[H][H].Br[CH2:19][CH2:20][CH2:21][N:22]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32]>CS(C)=O.O>[C:1]1([N:7]([CH2:19][CH2:20][CH2:21][N:22]2[C:26](=[O:27])[C:25]3=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]3[C:23]2=[O:32])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

7

反応物 4

HCID 21611N-3-BromopropylphthalimideHCID 24758Sodium hydrideHCID 81130N-2-PyridylanilineHCID 178418361HCID 178418361、化合物

生成物 1

HCID 20186606N-[3-(N-phenyl-N-pyrid-2-ylamino)propyl]phthalimide

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒3 回HCID 962Water溶媒

反応条件

温度
85 °C

実験手順

A solution of 2-(N-phenylamino)pyridine (5.0 g) in DMSO (15 ml) was added to a suspension of sodium hydride (0.78 g) in DMSO (20 ml). The mixture was stirred and slowly heated under nitrogen to 85° C. After the evolution of hydrogen had ceased, the mixture was cooled to room temperature and a solution of N-(3-bromopropyl)phthalimide (7.88 g) in DMSO (15 ml) added dropwise. The mixture was allowed to stand overnight and then poured into water. The aqueous phase was made acid to a pH between 2 to 4 and extracted with ether. The extracts were dried (MgSO4), the ether evaporated and the residue crystallised from ethanol to give N-[3-(N-phenyl-N-pyrid-2-ylamino)propyl]phthalimide, 3.69 g (35%) m.p. 103°-105° C.

後処理

  1. temperaturethe mixture was cooled to room temperature
  2. extractionextracted with ether
  3. dry with materialThe extracts were dried (MgSO4)
  4. customthe ether evaporated
  5. customthe residue crystallised from ethanol

出典と根拠

ORDレコード
ord-ef1965a29c304b348a573de56f31640e
出典データセット
uspto-grants-1987_09
特許番号
US04692456

反応ノート

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