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

HRID 485041

반응식

HRID 485041 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 202713332-(N-methyl-N-propynylamino)benzothiazole수율 84%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-655eb8d90eae40d1a7ee035d7ffa7030
출처 데이터셋
uspto-grants-1985_08
특허 번호
US04535088

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