Benzenesulfonyl chloride → methyl 3-[(phenylsulfonyl)amino]thiophene-2-carboxylate

HRID 2251311Notes

Reaction equation

HRID 2251311 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].[C:11]1([S:17](Cl)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>N1C=CC=CC=1.C(OCC)(=O)C>[CH3:10][O:9][C:7]([C:3]1[S:4][CH:5]=[CH:6][C:2]=1[NH:1][S:17]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:19])=[O:18])=[O:8]

Participants

5

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 89652Methyl 3-amino-2-thiophenecarboxylate

Product 1

HCID 4430392methyl 3-[(phenylsulfonyl)amino]thiophene-2-carboxylateYield 92.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 3-aminothiophene-2-carboxylate (3.14 g, 20 mmol) was dissolved in pyridine (10 mL) at room temperature. The flask was sealed with a septum and a nitrogen inlet. The solution was treated slowly with a benzenesulfonyl chloride (2.5 mL, 19.5 mmol). The reaction was followed by thin layer chromatography. The reaction was diluted with ethyl acetate and washing with 2N HCl. The organic layer was washed with saturated, aqueous sodium chloride solution and dried over sodium sulfate. The solution was decanted and evaporated under reduced pressure to give 3-benzenesulfonylaminothiophene-2-carboxylic acid methyl ester (5.36 g, 90%), which was used without further purification.

Workup

  1. customThe flask was sealed with a septum and a nitrogen inlet
  2. washwashing with 2N HCl
  3. washThe organic layer was washed with saturated, aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customThe solution was decanted
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b92ef40d467a4d37b862adf51971201d
Source dataset
uspto-grants-2008_01
Patent number
US07319111B2

Reaction notes

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