Triethylamine → Methyl 3-(3-aminophenylthiomethyl)thiophene-2-carboxylate

HRID 322228Notes

Reaction equation

HRID 322228 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.Br[CH2:17][C:18]1[CH:22]=[CH:21][S:20][C:19]=1[C:23]([O:25][CH3:26])=[O:24].C(=O)([O-])O.[Na+]>ClCCl>[NH2:1][C:2]1[CH:3]=[C:4]([S:8][CH2:17][C:18]2[CH:22]=[CH:21][S:20][C:19]=2[C:23]([O:25][CH3:26])=[O:24])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 315773-AminothiophenolHCID 516892Sodium BicarbonateHCID 10537693Methyl 3-(bromomethyl)thiophene-2-carboxylate

Product 1

HCID 15524292Methyl 3-(3-aminophenylthiomethyl)thiophene-2-carboxylateYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-aminothiophenol (2.3 g, 18.7 mmol) and triethylamine (3.12 ml, 22.4 mmol) in dichloromethane (30 ml) was slowly added methyl 3-bromomethylthiophene-2-carboxylate (6.24 g, 22.4 mmol) under ice-cooling, followed by stirring for 30 minutes. After the reaction was completed, a saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture. The organic layer was washed successively with a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained oily substance was purified by silica gel column chromatography (hexane/ethyl acetate=7/1) to give oily methyl 3-(3-aminophenylthiomethyl)thiophene-2-carboxylate (4.82 g, 92%).

Workup

  1. temperaturecooling
  2. washThe organic layer was washed successively with a saturated aqueous solution of sodium hydrogen carbonate
  3. dry with materiala saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate
  4. filtrationAfter the drying agent was filtered off
  5. concentrationthe organic layer was concentrated under reduced pressure
  6. customThe obtained oily substance was purified by silica gel column chromatography (hexane/ethyl acetate=7/1)

Sources & evidence

ORD record
ord-d51078036d904aeebe883fea751bea90
Source dataset
uspto-grants-2001_04
Patent number
US06211227B1

Reaction notes

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