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

HRID 385694노트

반응식

HRID 385694 반응식
[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

참가 물질

7

반응물 2

HCID 120273N-Iodosuccinimide2회HCID 59525796Benzyl[3-(aminocarbonyl)-2-thienyl]carbamate

생성물 1

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

시약·촉매·용매 4

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매HCID 14798Sodium Hydroxide용매HCID 24477Sodium Thiosulfate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dfc453da18ff48888508b1b902ef62e4
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367706B2

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