Chlorosuccinimide → 2-(N-Boc-amino)-5-chloro-3-phenyl-thiophene

HRID 1639524Notes

Reaction equation

HRID 1639524 reaction equation
[C:1]([NH:8][C:9]1[S:10][CH:11]=[CH:12][C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Cl:20]N1C(=O)CCC1=O>ClCCl>[C:1]([NH:8][C:9]1[S:10][C:11]([Cl:20])=[CH:12][C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 589118012-(N-Boc-amino)-3-phenyl-thiophene

Product 1

HCID 589117542-(N-Boc-amino)-5-chloro-3-phenyl-thiopheneYield 66.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 2-(N-Boc-amino)-3-phenyl-thiophene (89 mg, 0.32 mmol) in dichloromethane (4 ml) at 0° C. was slowly added N-chlorosuccinimide (48 mg, 0.36 mmol), and the mixture allowed warm to ambient temperature for 16 hr. The mixture was diluted with dichloromethane, washed with water, and the organic phase concentrated in vacuo. Flash chromatography on silica gel (ethyl acetate/hexanes) yielded 2-(N-Boc-amino)-5-chloro-3-phenyl-thiophene (66 mg, 66%).

Workup

  1. customat 0° C.
  2. washwashed with water
  3. concentrationthe organic phase concentrated in vacuo

Sources & evidence

ORD record
ord-cba25e849d204f5f8a3ba379e1775efe
Source dataset
uspto-grants-2012_02
Patent number
US08110568B2

Reaction notes

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