Ethyl Acetate → ethyl N-[2-(4-chlorophenyl)ethyl]carbamate

HRID 1843818Notes

Reaction equation

HRID 1843818 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][NH2:16])=[CH:10][CH:9]=1.[CH2:17]([O:19][C:20](=[O:22])C)[CH3:18]>C(Cl)(Cl)Cl.CCCCCC>[CH2:17]([O:19][C:20](=[O:22])[NH:16][CH2:15][CH2:14][C:11]1[CH:12]=[CH:13][C:8]([Cl:7])=[CH:9][CH:10]=1)[CH3:18]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 674302-(4-Chlorophenyl)ethylamine

Product 1

HCID 15405334ethyl N-[2-(4-chlorophenyl)ethyl]carbamateYield 52.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8058HexaneSolvent

Procedure

Chloro ethyl formate (1.92 mL) and 2N Na2CO3 solution (20 mL) were added to a stirred solution of 2-(4-chloro-phenyl)-ethylamine (I-1b: 2.6 g, 0.01667 mmol) in chloroform (20 mL). The resulting mixture was stirred at room temperature for 3 hours. The reaction was monitored by TLC (20% ethylacetate in hexane). The reaction mixture was partitioned between water and chloroform. The organic layer was washed with water, brine solution, dried over Na2SO4 and concentrated under reduced pressure. Purification by column chromatography on silica gel (10% ethylacetate in hexane) afforded 2 g of the product (52.6% yield).

Workup

  1. customThe reaction mixture was partitioned between water and chloroform
  2. washThe organic layer was washed with water, brine solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customPurification by column chromatography on silica gel (10% ethylacetate in hexane)

Sources & evidence

ORD record
ord-9cd895e1260b47a38771098e81a67422
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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