Triethylamine → 2-Propionylthioquinoline

HRID 1490346노트

반응식

HRID 1490346 반응식
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1[SH:16].C(N(CC)CC)C>C(Cl)Cl>[C:1]([S:16][C:7]1[CH:8]=[CH:9][C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:6]=1)(=[O:4])[CH2:2][CH3:3]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 178418736HCID 178418736, 화합물

생성물 1

HCID 196989512-Propionylthioquinoline수율 53.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

480 mg (1.2 equivalents) of propionyl chloride were added, whilst ice-cooling, to a solution of 1 g of 2-quinolinethiol and 0.83 ml (1.2 equivalents) of triethylamine in 20 ml of anhydrous methylene chloride, and the resulting mixture was stirred for 30 minutes. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was mixed with ethyl acetate. This mixture was washed twice with a dilute aqueous solution of sodium hydrogencarbonate and was then washed with water. The organic layer was separated and dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure. The residue was purified by flash chromatography through silica gel, using a 1:1 by volume mixture of cyclohexane and ethyl acetate as the eluent, to give 600 mg of the title compound having an Rf value of 0.4.

후처리

  1. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  2. additionthe resulting residue was mixed with ethyl acetate
  3. washThis mixture was washed twice with a dilute aqueous solution of sodium hydrogencarbonate
  4. washwas then washed with water
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed by distillation under reduced pressure
  8. customThe residue was purified by flash chromatography through silica gel
  9. additionby volume mixture of cyclohexane and ethyl acetate as the eluent

출처 및 근거

ORD 기록
ord-26e5d5b9ff174b05a24183212385c89d
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05681951

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