2,4,6-Trimethylpyridine → HCID 90426276, compound

HRID 718153Notes

Reaction equation

HRID 718153 reaction equation
Cl.[CH:2]1([C:8](=[NH:12])[O:9][CH2:10][CH3:11])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.N1C(C)=CC(C)=CC=1C.Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24]>>[CH2:26]([O:25][C:23]([N:12]=[C:8]([CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1)[O:9][CH2:10][CH3:11])=[O:24])[CH3:27]

Participants

4

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 10928Ethyl chloroformateHCID 12270050HCID 12270050, compound

Product 1

HCID 90426276HCID 90426276, compoundYield 96%

Conditions

Temperature
0 °C

Procedure

Ethyl cyclohexanecarbimidate hydrochloride (1.8 g, 9.2 mmol) was suspended in hexanes (22.9 mL) and cooled to 0° C. 2,4,6-Collidine (4.1 mL, 30.9 mmol) and ethyl chloroformate (1.9 g, 17.8 mmol) were sequentially added and the mixture was allowed to warm to RT and stirred for 12 h. The solvent was removed in vacuo. The residue was suspended in EtOAc (50 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-ethoxycarbonylcyclohexanecarbimidate (2.0 g, 96%) as a yellow amorphous solid. 1H NMR (400 MHz, DMSO-d6): δ 4.09 (q, J=7.1 Hz, 2H), 4.02 (q, J=7.1 Hz, 2H), 2.41-2.31 (m, 1H), 1.70-1.65 (m, 4H), 1.40-1.36 (m, 2H), 1.26-1.09 (m, 4H), 1.19 (t, J=7.1 Hz, 6H).

Workup

  1. temperatureto warm to RT
  2. customThe solvent was removed in vacuo
  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-99978a7c9c8a425991119a363223cec7
Source dataset
uspto-grants-2015_11
Patent number
US09193719B2

Reaction notes

Loading…