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

HRID 1534618ノート

反応式

HRID 1534618 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 126670543-(Naphth-2-ylthio)propiophenone収率 22.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3feff9f4105649b3a60f2d7dec1ba684
出典データセット
uspto-grants-1992_02
特許番号
US05089513

反応ノート

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