2-Thiophenecarboxylic acid → HCID 47222443, compound

HRID 397049

Reaction equation

HRID 397049 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6][CH2:7][NH2:8].[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17](O)=[O:18].O.ON1C2C=CC=CC=2N=N1.Cl.C(N(CC)CCCN=C=NCC)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][CH2:7][NH:8][C:17]([C:13]2[S:12][CH:16]=[CH:15][CH:14]=2)=[O:18])[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 107002-Thiophenecarboxylic acidHCID 748663-MethoxyphenethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 99645121-(3-Diethylaminopropyl)-3-ethylcarbodiimide hydrochloride

Product 1

HCID 47222443HCID 47222443, compoundYield 107.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3-methoxyphenethylamine (1.000 g, 6.61 mmol), 2-thiophenecarboxylic acid (0.847 g, 6.61 mmol), 1-hydroxybenzotriazole hydrate (1.340 g, 9.92 mmol), and 1-(3-diethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.330 g, 6.94 mmol) in anhydrous CH2Cl2 (20 ml) was stirred at 0° C. under N2 for 1 hr, then warmed to rt and stirred at rt for 18 hr. The reaction mixture was washed with 1M NaOH (10 ml) followed by 1M HCl (10 ml), dried over MgSO4, and concentrated in vacuo to give 1.859 g of yellow oil. Purification by flash chromatography, eluting with hexane:EtOAc (7:3) gave 1.637 g (95% yield) of yellow oil.

Workup

  1. temperaturewarmed to rt
  2. stirringstirred at rt for 18 hr
  3. washThe reaction mixture was washed with 1M NaOH (10 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-383e5819d9164389b3de5122ca6e2c14
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Linked notes

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