Triethylamine → Rac-4-(2-chloro-propionylamino)-thiophene-3-carboxylic acid methyl ester

HRID 14611

Reaction equation

HRID 14611 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:9]([NH2:10])=[CH:8][S:7][CH:6]=1)=[O:4].[Cl:11][CH:12]([CH3:16])[C:13](Cl)=[O:14].C(N(CC)CC)C>ClCCl>[CH3:1][O:2][C:3]([C:5]1[C:9]([NH:10][C:13](=[O:14])[CH:12]([Cl:11])[CH3:16])=[CH:8][S:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1110192-Chloropropionyl chlorideHCID 2777610Methyl 4-aminothiophene-3-carboxylate

Product 1

HCID 68688356Rac-4-(2-chloro-propionylamino)-thiophene-3-carboxylic acid methyl esterYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-15 °C

Procedure

To a suspension of 4-amino-thiophene-3-carboxylic acid methyl ester (2.0g) in dichloromethane (25 mL) was added 2-chloropropionyl chloride (1.13 mL). The reaction mixture was then cooled down to −15° C. and a solution of triethylamine (3.2 mL) in dichloromethane (5 mL) was slowly added over 30 minutes. After such time the reaction mixture was allowed to warm up to room temperature, and the solution was washed twice with water, dried over sodium sulfate and then concentrated in vacuo. The residue was purified by column chromatography to yield the title compound as a light yellow solid (2.1g, 82%). MS (EI): 247.0.

Workup

  1. temperatureto warm up to room temperature
  2. washthe solution was washed twice with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-b604834c7358483795593421fbc68b98
Source dataset
uspto-grants-2010_06
Patent number
US07732452B2

Linked notes

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