2-Methoxyethylamine → HCID 2143474, compound

HRID 75546Notes

Reaction equation

HRID 75546 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].[C:6]([N:14]=[C:15]=[S:16])(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:15]([NH:14][C:6](=[O:13])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[S:16]

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 68284Benzoyl isothiocyanate

Product 1

HCID 2143474HCID 2143474, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methoxyethylamine (17.7 mL, 202.2 mmol) was added dropwise over 30 minutes to a stirring solution of benzoylisothiocyanate (30.00 g, 183.8 mmol) in CH2Cl2 (300 mL) at room temperature under argon and the mixture was stirred at room temperature for 16 hours. The mixture was washed sequentially with 10% aqueous citric acid (75 mL), water (75 mL) and brine (75 mL), dried over MgSO4 and concentrated in vacuo. The resulting yellow oil solidified on standing to give the title compound (41.85 g, 96%). The material was used directly in the next step without further purification.

Workup

  1. washThe mixture was washed sequentially with 10% aqueous citric acid (75 mL), water (75 mL) and brine (75 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5e5ddd0135c14e0f9068699cd3b48918
Source dataset
uspto-grants-2014_09
Patent number
US08835449B2

Reaction notes

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