1-Benzofuran-2-sulfonyl chloride → HCID 71714789, compound

HRID 70468Notes

Reaction equation

HRID 70468 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13].[O:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH:18]=[C:17]1[S:25](Cl)(=[O:27])=[O:26]>N1C=CC=CC=1.CCOC(C)=O>[O:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH:18]=[C:17]1[S:25]([NH:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])(=[O:27])=[O:26]

Participants

5

Reactant 2

HCID 27951721-Benzofuran-2-sulfonyl chlorideHCID 43617660HCID 43617660, compound

Product 1

HCID 71714789HCID 71714789, compoundYield 52.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 3-((2-amino-4-chlorophenyl)thio)propanoate (412 mg, 1.67 mmol) in pyridine (2 ml) was added 1-benzofuran-2-sulfonyl chloride (363 mg, 1.67 mmol). The reaction was stirred at room temperature for 72 hours, diluted with EtOAc and extracted with HCl, brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (10-20% EtOAc in hexane) to yield the title compound (373 mg, 52%).

Workup

  1. extractionextracted with HCl, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel (10-20% EtOAc in hexane)

Sources & evidence

ORD record
ord-2e6d7fcdaa8c4d14810b9e84300f1ff5
Source dataset
uspto-grants-2014_09
Patent number
US08822530B2

Reaction notes

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