Aniline → HCID 3726134, compound

HRID 2105281Notes

Reaction equation

HRID 2105281 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:15]([C:19]1[S:20][CH:21]=[CH:22][C:23]=1[S:24](Cl)(=[O:26])=[O:25])([O:17][CH3:18])=[O:16]>C1COCC1>[CH3:18][O:17][C:15]([C:19]1[S:20][CH:21]=[CH:22][C:23]=1[S:24](=[O:26])(=[O:25])[NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:16]

Participants

5

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 27367332-Thiophenecarboxylic acid, 3-(chlorosulfonyl)-, methyl ester

Product 1

HCID 3726134HCID 3726134, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of an aniline (1.02 g, 10.9 mmol, 11.1 equivalents) dissolved in dry THF (35 mL) and triethylamine (1.53 mL, 1.1 equivalents) at room temperature, sealed with a septum and a nitrogen inlet, was added 2-carbomethoxythiophene-3-sulfonyl chloride (2.5 g, 9.9 mmol, 95% purity). The reaction mixture was stirred at room temperature over night. Upon completion, the reaction will be extracted by diluting with ethyl acetate and washing with aqueous HCl (2N), water and saturated, aqueous sodium chloride solution. The organic layer was dried over sodium sulfate. The solution will be decanted and evaporated under reduced pressure to give the desired 3-phenylsulfamoylthiophene-2-carboxylic acid methyl ester (2.6 g, 88%).

Workup

  1. customUpon completion, the reaction
  2. extractionwill be extracted
  3. additionby diluting with ethyl acetate
  4. washwashing with aqueous HCl (2N), water
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customThe solution will be decanted
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-eda5c0d9a19744a6a139c574be64ba23
Source dataset
uspto-grants-2009_08
Patent number
US07579340B2

Reaction notes

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