tert-Butylsulfinamide, (R)-(+)- → (NE)-N-[(2-chloro-3-fluorophenyl)methylidene]-2-methylpropane-2-sulfinamide

HRID 80534

反応式

HRID 80534 の反応式
[Cl:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:11][C:12]([S@:15]([NH2:17])=[O:16])([CH3:14])[CH3:13]>ClCCl.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Cl:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:3]=1/[CH:4]=[N:17]/[S:15]([C:12]([CH3:14])([CH3:13])[CH3:11])=[O:16]

参加物

5

反応物 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 149449052-Chloro-3-fluorobenzaldehyde

生成物 1

HCID 88924234(NE)-N-[(2-chloro-3-fluorophenyl)methylidene]-2-methylpropane-2-sulfinamide

試薬・触媒・溶媒 2

HCID 11026Titanium isopropoxide触媒HCID 6344Dichloromethane溶媒

実験手順

2-Chloro-3-fluorobenzaldehyde (2.5 g) and (R)-(+)-2-methyl-2-propanesulfinamide were dissolved in dichloromethane (50 ml), and then titanium(IV) isopropoxide (23.6 ml) was added. The mixture was heated for three hours under reflux, then poured onto ice (150 g) and stirred vigorously for ten minutes. The mixture was filtered through kieselguhr and the filtrate was extracted with dichloromethane (3×50 ml). The organic phase was dried (Na2SO4), filtered and concentrated under reduced pressure. The product (4 g) was used further without further purification.

後処理

  1. temperatureThe mixture was heated for three hours
  2. temperatureunder reflux
  3. additionpoured onto ice (150 g)
  4. filtrationThe mixture was filtered through kieselguhr
  5. extractionthe filtrate was extracted with dichloromethane (3×50 ml)
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe product (4 g) was used further without further purification

出典と根拠

ORDレコード
ord-77f803d76031470495a65644be01caf6
出典データセット
uspto-grants-2014_09
特許番号
US08846666B2

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