2-Naphthalenethiol → 3-(Naphth-2-ylthio)propiophenone

HRID 1534618노트

반응식

HRID 1534618 반응식
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[SH:11].Br[CH2:13][CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:16].[OH-].[Na+]>CN(C)C=O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11][CH2:13][CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:16]

참가 물질

5

반응물 3

HCID 70582-NaphthalenethiolHCID 14798Sodium HydroxideHCID 1224323-Bromo-1-phenylpropan-1-one

생성물 1

HCID 126670543-(Naphth-2-ylthio)propiophenone수율 22.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 2-naphthalenethiol (12.94 g), 3-bromopropiophenone (17.35 g), cuprous oxide (5.83 g), sodium hydroxide (3.24 g) and dimethylformamide (130 ml) was heated to reflux for 18 hours. The mixture was concentrated and the residue was partitioned between diethyl ether and water. The organic phase was dried (MgSO4) and evaporated. The residue was dissolved in a mixture of ethyl acetate and hexane and treated with charcoal. The solution was filtered and evaporated. The residue was recrystallised from a mixture of methanol and water to give 3-(naphth-2-ylthio)propiophenone (5.23 g, 22%), m.p. 90°-91° C.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 18 hours
  3. concentrationThe mixture was concentrated
  4. customthe residue was partitioned between diethyl ether and water
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customevaporated
  7. dissolutionThe residue was dissolved in a mixture of ethyl acetate and hexane
  8. additiontreated with charcoal
  9. filtrationThe solution was filtered
  10. customevaporated
  11. customThe residue was recrystallised from a mixture of methanol and water

출처 및 근거

ORD 기록
ord-3feff9f4105649b3a60f2d7dec1ba684
출처 데이터셋
uspto-grants-1992_02
특허 번호
US05089513

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