Carbonochloridate → HCID 68828269, compound

HRID 1453965Notes

Reaction equation

HRID 1453965 reaction equation
C[N:2]1[CH2:11][CH2:10][C:9]2([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=3)[C:4]([CH3:20])([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:3]1.ClC([O-])=O>ClCCCl>[CH3:19][O:18][C:14]1[CH:13]=[C:12]([C:9]23[CH2:8][CH2:7][CH2:6][CH2:5][C:4]2([CH3:20])[CH2:3][NH:2][CH2:11][CH2:10]3)[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 21226386CarbonochloridateHCID 68828065HCID 68828065, compound

Product 1

HCID 68828269HCID 68828269, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 430 mg (1.59 mmol) of 9 in anhydrous 1,2-dichloroethane (15 mL) at reflux was added 250 mg (1.75 mmol) of 1-chloethyl chloroformate drop wise. The resulting solution was heated under reflux for 20 h and then cooled to room temperature. The mixture was washed with saturated sodium bicarbonate solution, water, the organic layer evaporated, and the resulting oil dissolved immediately in methanol and refluxed overnight. After cooling to room temperature, the methanol was removed under reduced pressure, and the residue was treated with saturated sodium bicarbonate solution. The mixture was extracted with 3:1, methylene chloride/THF, and the combined organic extracts were washed once with water. Removal of a solvent provided 0.36 g (89%) of crude 10 as yellow oil: 1H NMR (300 MHz, CDCl3) δ 1.04 [s, 3H], 2.45-1.43 [m, 13H], 3.06 [m, 2H], 3.80 [s, 3H], 6.76 [m, 1H], 6.98 [m, 3H]; 13CNMR (300 MHz, CDCl3) δ 159.0, 128.3, 122.2, 116.9, 110.0, 55.6, 55.5, 43.8, 43.5, 36.4, 35.3, 30.7, 24.4, 22.4, 21.9

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureunder reflux for 20 h
  3. washThe mixture was washed with saturated sodium bicarbonate solution, water
  4. customthe organic layer evaporated
  5. dissolutionthe resulting oil dissolved immediately in methanol
  6. temperaturerefluxed overnight
  7. temperatureAfter cooling to room temperature
  8. customthe methanol was removed under reduced pressure
  9. additionthe residue was treated with saturated sodium bicarbonate solution
  10. extractionThe mixture was extracted with 3:1, methylene chloride/THF
  11. washthe combined organic extracts were washed once with water
  12. customRemoval of a solvent

Sources & evidence

ORD record
ord-6580320ab6964a488a00c37878f191aa
Source dataset
uspto-grants-2009_01
Patent number
US07476679B2

Reaction notes

Loading…