Methylamine → 4-(Bromomethyl)-N-methylbenzenesulfonamide

HRID 2041110ノート

反応式

HRID 2041110 の反応式
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:19][NH2:20]>C1COCC1>[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:20][CH3:19])(=[O:11])=[O:10])=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 6329MethylamineHCID 11430Potassium CarbonateHCID 27344094-(Bromomethyl)benzenesulfonyl chloride

生成物 1

HCID 100156454-(Bromomethyl)-N-methylbenzenesulfonamide収率 71%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Mix 4-(bromomethyl)benzenesulfonyl chloride (2.7 g, 10 mmol), anhydrous potassium carbonate (1.4 g, 10 mmol) and anhydrous THF (60 mL) under nitrogen. Cool the mixture in an ice bath, add dropwise a 2M solution of methylamine in THF, and stir at this temperature for 30 min. Remove the ice bath and stir at ambient temperature for 16 h. Dilute with EtOAc then wash with 1N aqueous HCl. Separate the organic layer, dry over Na2SO4 and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 4:1, 7:3 and 13:7) to obtain the title compound (1.5 g, 71%). MS (ES+) m/z: 266 (M+H)+.

後処理

  1. temperatureCool the mixture in an ice bath
  2. customRemove the ice bath
  3. stirringstir at ambient temperature for 16 h
  4. additionDilute with EtOAc
  5. washthen wash with 1N aqueous HCl
  6. customSeparate the organic layer
  7. dry with materialdry over Na2SO4
  8. concentrationconcentrate in vacuo
  9. customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 4:1, 7:3 and 13:7)

出典と根拠

ORDレコード
ord-9c3706d5bf73455f8f178b2559803b28
出典データセット
uspto-grants-2013_11
特許番号
US08580780B2

反応ノート

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