Ethyl chloroformate → ethyl N-ethoxycarbonyl-2-phenylacetimidate

HRID 718147Notes

Reaction equation

HRID 718147 reaction equation
Cl.[C:2]1([CH2:8][C:9](=[NH:13])[O:10][CH2:11][CH3:12])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:15]([O:17][CH2:18][CH3:19])=[O:16]>C(Cl)Cl.CCOC(C)=O>[CH2:18]([O:17][C:15]([N:13]=[C:9]([O:10][CH2:11][CH3:12])[CH2:8][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:16])[CH3:19]

Participants

5

Reactant 2

HCID 10928Ethyl chloroformateHCID 12218775Ethyl 2-phenylacetimidate hydrochloride

Product 1

HCID 101005605ethyl N-ethoxycarbonyl-2-phenylacetimidateYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 2-phenylacetimidate hydrochloride (1.7 g, 8.5 mmol) was dissolved in DCM (10.6 mL) and cooled to 0° C. TEA (7.1 mL, 51.1 mmol) was added dropwise the mixture was stirred for 1 h. Ethyl chloroformate (1.6 g, 14.8 mmol) was added and the reaction mixture was allowed to warm to RT and stirred for 12 h. The mixture was diluted with EtOAc (100 mL) and the solids were removed by filtration through diatomaceous earth. The filter cake was washed with EtOAc (3×10 mL) and the combined filtrates were concentrated in vacuo to afford ethyl N-ethoxycarbonyl-2-phenylacetimidate (1.9 g, 93%) as a yellow oil. 1H NMR (400 MHz, DMSO-d6): δ 7.27-7.26 (m, 5H), 4.01-4.00 (m, 4H), 3.70 (s, 2H), 1.18-1.08 (m, 6H).

Workup

  1. temperatureto warm to RT
  2. stirringstirred for 12 h
  3. customthe solids were removed by filtration through diatomaceous earth
  4. washThe filter cake was washed with EtOAc (3×10 mL)
  5. concentrationthe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-5338b3930de24ed7a7acc09de8d647df
Source dataset
uspto-grants-2015_11
Patent number
US09193719B2

Reaction notes

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