Ethyl chloroformate → HCID 68489720, compound

HRID 389039Notes

Reaction equation

HRID 389039 reaction equation
[C:1](Cl)(=[O:5])[O:2][CH2:3][CH3:4].[Br:7][C:8]1[S:9][C:10]2[CH2:11][CH2:12][C:13]3[CH:28]=[CH:27][CH:26]=[CH:25][C:14]=3[C:15](=[C:18]3[CH2:23][CH2:22][N:21](C)[CH2:20][CH2:19]3)[C:16]=2[CH:17]=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Br:7][C:8]1[S:9][C:10]2[CH2:11][CH2:12][C:13]3[CH:28]=[CH:27][CH:26]=[CH:25][C:14]=3[C:15](=[C:18]3[CH2:23][CH2:22][N:21]([C:1]([O:2][CH2:3][CH3:4])=[O:5])[CH2:20][CH2:19]3)[C:16]=2[CH:17]=1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 68491393HCID 68491393, compound

Product 1

HCID 68489720HCID 68489720, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl chlorocarbonate (32 mL, 336 mmol) was added to a toluene (200 mL) solution of the compound obtained in Example 1 (21.0 g, 56 mmol), and the mixture was refluxed while heating for 6 hours. The mixture was allowed to cool in the air, and the reaction mixture was added to a saturated aqueous sodium hydrogencarbonate solution to allow the separation of an organic layer. The organic layer was washed with a saturated sodium chloride solution and dried over anhydrous sodium sulfate, the solvents were then distilled off under a reduced pressure, and the residue was purified by column chromatography (hexane:ethyl acetate=19:1), to give 15.0 g (62%) of the captioned compound in the form of an oily product.

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewhile heating for 6 hours
  3. temperatureto cool in the air
  4. customthe separation of an organic layer
  5. washThe organic layer was washed with a saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvents were then distilled off under a reduced pressure
  8. customthe residue was purified by column chromatography (hexane:ethyl acetate=19:1)

Sources & evidence

ORD record
ord-104f4fdd6ea14a8e9acd95e614d01dfb
Source dataset
uspto-grants-2013_02
Patent number
US08377967B2

Reaction notes

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