(2-Thienylmethyl)amine → HCID 4293, compound

HRID 1489825Notes

Reaction equation

HRID 1489825 reaction equation
[S:1]([C:5]1[S:9][C:8]([S:10](Cl)(=[O:12])=[O:11])=[CH:7][CH:6]=1)(=[O:4])(=[O:3])[NH2:2].[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[CH2:19][NH2:20]>C(O)C>[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[CH2:19][NH:20][S:10]([C:8]1[S:9][C:5]([S:1]([NH2:2])(=[O:4])=[O:3])=[CH:6][CH:7]=1)(=[O:11])=[O:12]

Participants

4

Reactant 2

HCID 34005(2-Thienylmethyl)amineHCID 22901925HCID 22901925, compound

Product 1

HCID 4293HCID 4293, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-sulfamoyl-thiophene-2-sulfonyl chloride (0.80 g, 3.1 mmol) in ethanol (10 mL) at 0° C. was added 2-thiophenemethylamine (0.67 mL, 6.51 mmol) and this mixture stirred at room temperature for 18 hr. After evaporation of solvent the residue was dissolved in ethyl acetate (200 mL) and this solution was washed with saturated aqueous sodium bicarbonate (2×50 mL), dried (MgSO4), and evaporated to a crude material which was purified by column chromatography (silica, 5% methanol/methylene chloride) and recrystallization [methanol/methylene chloride (1:50)] to give the desired product (450 mg, 45%): mp 146°-148° C. Analysis: Calculated for C9H10 N2O4S4 : C, 31.94; H, 2.98; N, 8.28. Found: C, 32.00; H, 2.96; N, 8.29.

Workup

  1. customAfter evaporation of solvent the residue
  2. dissolutionwas dissolved in ethyl acetate (200 mL)
  3. washthis solution was washed with saturated aqueous sodium bicarbonate (2×50 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated to a crude material which
  6. customwas purified by column chromatography (silica, 5% methanol/methylene chloride) and recrystallization [methanol/methylene chloride (1:50)]

Sources & evidence

ORD record
ord-51c9bf7118fa460d92a98189ac58ce70
Source dataset
uspto-grants-1997_10
Patent number
US05679670

Reaction notes

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