N-Iodosuccinimide → Benzyl[3-(aminocarbonyl)-5-iodo-2-thienyl]carbamate

HRID 385694ノート

反応式

HRID 385694 の反応式
[CH2:1]([O:8][C:9](=[O:19])[NH:10][C:11]1[S:12][CH:13]=[CH:14][C:15]=1[C:16]([NH2:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:20]N1C(=O)CCC1=O>ClCCl.C(OCC)(=O)C.S([O-])([O-])(=O)=S.[Na+].[Na+].[OH-].[Na+]>[CH2:1]([O:8][C:9](=[O:19])[NH:10][C:11]1[S:12][C:13]([I:20])=[CH:14][C:15]=1[C:16]([NH2:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 2

HCID 120273N-Iodosuccinimide2 回HCID 59525796Benzyl[3-(aminocarbonyl)-2-thienyl]carbamate

生成物 1

HCID 59525870Benzyl[3-(aminocarbonyl)-5-iodo-2-thienyl]carbamate

試薬・触媒・溶媒 4

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒HCID 14798Sodium Hydroxide溶媒HCID 24477Sodium Thiosulfate溶媒

実験手順

To a solution of benzyl[3-(aminocarbonyl)-2-thienyl]carbamate (4.39 g, 15.88 mmol) in dichloromethane (440 mL) was added N-iodosuccinimide (3.57 g, 15.88 mmol). An additional amount of N-iodosuccinimide (1.07 g) was added in 3 portions over the next 60 min to drive the reaction to completion. The dark reaction mixture was diluted with ethyl acetate (700 mL), hexanes (100 mL), aqueous sodium thiosulfate (1 M, 150 mL), and aqueous sodium hydroxide (1 M, 300 mL). The layers were separated, and the organic layer was washed with saturated aqueous sodium bicarbonate (100 mL) and brine (150 mL), dried over sodium sulfate, filtered, and concentrated to afford the title compound as a solid.

後処理

  1. customthe reaction to completion
  2. customThe dark reaction mixture
  3. customThe layers were separated
  4. washthe organic layer was washed with saturated aqueous sodium bicarbonate (100 mL) and brine (150 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-dfc453da18ff48888508b1b902ef62e4
出典データセット
uspto-grants-2013_02
特許番号
US08367706B2

反応ノート

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