Propargyl bromide → 2-(N-methyl-N-propynylamino)benzothiazole

HRID 485041

反応式

HRID 485041 の反応式
[CH3:1][NH:2][C:3]1[S:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[CH3:12][CH2:13][CH2:14]CCC.C([Li])CCC.C(Br)C#C>O1CCCC1.C(Cl)(Cl)Cl>[CH3:1][N:2]([C:3]1[S:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1)[C:12]#[C:13][CH3:14]

参加物

7

反応物 4

HCID 7842Propargyl bromideHCID 8058HexaneHCID 28160N-Methylbenzothiazol-2-amineHCID 178418339Butyllithium

生成物 1

HCID 202713332-(N-methyl-N-propynylamino)benzothiazole収率 84%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

2-Methylaminobenzothiazole (c) (14.0 g) was dissolved in anhydrous tetrahydrofuran (250 ml) and a hexane solution (73 ml) of butyl lithium (6.53 g) was added thereto at -78° C. with stirring. The mixture was stirred for 1.5 hours under cooling and 2-propynyl bromide (8.4 ml) was dropwise added thereto. The resultant mixture was allowed to stand at room temperature overnight and then evaporated to remove the solvent. After addition of water, the residue was extracted with ether. The extract was washed with water, dried and evaporated to remove the solvent. The resultant residue was applied to column chromatography on silica gel (280 g) to give 2-(N-methyl-N-propynylamino)benzothiazole (d) (14.5 g, yield 84%) from chloroform eluate.

後処理

  1. stirringThe mixture was stirred for 1.5 hours
  2. temperatureunder cooling
  3. customevaporated
  4. customto remove the solvent
  5. additionAfter addition of water
  6. extractionthe residue was extracted with ether
  7. washThe extract was washed with water
  8. customdried
  9. customevaporated
  10. customto remove the solvent

出典と根拠

ORDレコード
ord-655eb8d90eae40d1a7ee035d7ffa7030
出典データセット
uspto-grants-1985_08
特許番号
US04535088

関連ノート

読み込み中…