Methyl chloroformate → HCID 86685923, compound

HRID 2277587Notes

Reaction equation

HRID 2277587 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH2:11])[CH:6]=[CH:7][CH:8]=1.[CH3:12]CN(CC)CC.Cl[C:20]([O:22][CH3:23])=[O:21]>C(Cl)Cl>[CH3:23][O:22][C:20](=[O:21])[NH:11][CH2:10][CH:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([Cl:2])[CH:4]=1)[CH3:12]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 5340733989042-13-7

Product 1

HCID 86685923HCID 86685923, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(3-chloro-phenyl)-ethylamine hydrochloride (6.22 g, 30.2 mmol) and Et3N (6.1 g, 60.4 mmol) in DCM (20 mL) was added methyl chloroformate (4.28 g, 45 mmol) dropwise at 0° C., and the resulting mixture was stirred at room temperature for 0.5 hour. The reaction mixture was then washed with water (3×10 mL), 1N HCl (10 mL) and brine (10 mL). The organic layer was dried over anhy. Na2SO4, filtered and concentrated in vacuo. The residue formed was dried in vacuo to give the title compound (5.5 g, 80%) as yellow oil. MS: 228.1 (M+H+).

Workup

  1. washThe reaction mixture was then washed with water (3×10 mL), 1N HCl (10 mL) and brine (10 mL)
  2. customThe organic layer was dried over anhy
  3. filtrationNa2SO4, filtered
  4. concentrationconcentrated in vacuo
  5. customThe residue formed
  6. customwas dried in vacuo

Sources & evidence

ORD record
ord-02b2881ecf464f048d6429465e278e26
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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