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

HRID 385694Notes

Reaction equation

HRID 385694 reaction equation
[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

Participants

7

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-dfc453da18ff48888508b1b902ef62e4
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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