Triethylamine → N-(2-(4-Methoxyphenylthio)ethyl)acrylamide

HRID 1917081Notes

Reaction equation

HRID 1917081 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:10][CH2:11][NH2:12])=[CH:5][CH:4]=1.[C:13](Cl)(=[O:16])[CH:14]=[CH2:15].C([O-])([O-])=O.[Na+].[Na+].C(N(CC)CC)C>CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:10][CH2:11][NH:12][C:13](=[O:16])[CH:14]=[CH2:15])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 13140Acryloyl chlorideHCID 12261932Ethanamine, 2-[(4-methoxyphenyl)thio]-

Product 1

HCID 57864668N-(2-(4-Methoxyphenylthio)ethyl)acrylamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound 1 (1.83 g) in EtOAc (50 mL) was added acryloyl chloride (1.35 g, 1.5 eq.) and Na2CO3 (2.12 g, 2.0 eq.). The reaction mixture was stirred at r.t. overnight and triethylamine was added. After stirring for 20 min, the mixture was washed with H2O (20 mL), 1N HCl (2×20 mL) and sat. NaHCO3 (2×20 mL). The solvents were removed by evaporation under reduced pressure to give product 32 as white solid (one spot on TLC). Yield: 2.2 g, 92.8%.

Workup

  1. stirringAfter stirring for 20 min
  2. washthe mixture was washed with H2O (20 mL), 1N HCl (2×20 mL) and sat. NaHCO3 (2×20 mL)
  3. customThe solvents were removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-2bc33929c3c049d2afdbcd4abc18d68f
Source dataset
uspto-grants-2013_12
Patent number
US08618282B2

Reaction notes

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