Triethylamine → 2-methylthio-2-imidazoline N-ethylcarbamate

HRID 378176

Reaction equation

HRID 378176 reaction equation
[CH3:1][S:2][C:3]1[NH:4][CH2:5][CH2:6][N:7]=1.I.[CH2:9]([N:11](CC)CC)[CH3:10].C([O:18][C:19](Cl)=[O:20])C>C(Cl)Cl>[CH3:1][S:2][C:3]1[NH:7][CH2:6][CH2:5][N:4]=1.[CH2:9]([NH:11][C:19](=[O:20])[O-:18])[CH3:10]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 24841Hydrogen iodideHCID 883692-Methylthio-2-imidazoline hydroiodide

Product 1

HCID 867551732-methylthio-2-imidazoline N-ethylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-methylthio-2-imidazoline.HI (Aldrich) (10 g, 0.041 mole) and triethylamine (8.3 g, 0.0082 mole) in CH2Cl2 (50 mL) was added ethylchloroformate (Aldrich) (4.5 g, 0.041 mole) dropwise at ice bath temperature. The reaction was stirred overnight at room temperature. The precipitate was filtered and washed with CH2Cl2. The CH2Cl2 from the filtrate was washed with H2O (3×), dried over MgSO4 and removed under vacuum to yield 2-methylthio-2-imidazoline-N-ethylcarbamate (7.1 g) as a clear yellow oil.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with CH2Cl2
  3. washThe CH2Cl2 from the filtrate was washed with H2O (3×)
  4. dry with materialdried over MgSO4
  5. customremoved under vacuum

Sources & evidence

ORD record
ord-f00a8f047563487b9aac4f53e5631c5c
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Linked notes

Loading…