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

HRID 874164Notes

Reaction equation

HRID 874164 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-5db90ad037c24a0fa03353e16b786d82
Source dataset
uspto-grants-2015_03
Patent number
US08980837B2

Reaction notes

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