Ethyl chloroformate → HCID 89262758, compound

HRID 2277741Notes

Reaction equation

HRID 2277741 reaction equation
[C:1](Cl)(=[O:5])[O:2][CH2:3][CH3:4].[CH3:7][S:8]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=1)(=[NH:10])=[O:9]>N1C=CC=CC=1>[CH2:3]([O:2][C:1](=[O:5])[N:10]=[S:8]([CH3:7])([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=1)=[O:9])[CH3:4]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 89239694HCID 89239694, compound

Product 1

HCID 89262758HCID 89262758, compoundYield 105.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ethyl chlorocarbonate (8.1 mL; 84.6 mmol) was added dropwise to a stirred solution of (rac)-1-[(S-methylsulfonimidoyl)methyl]-3-nitrobenzene (13.9 g; 65.1 mmol) in pyridine (615 mL) at 0° C. The batch was slowly warmed to room temperature. After 24 hours the batch was concentrated and the residue was dissolved in ethyl acetate and washed with saturated aqueous sodium chloride solution. The organic phase was filtered using a Whatman filter and concentrated to give the desired product (19.7 g) that was used without further purification.

Workup

  1. concentrationAfter 24 hours the batch was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with saturated aqueous sodium chloride solution
  4. filtrationThe organic phase was filtered
  5. filtrationfilter
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0cf3a13a04b242358605b44e84b80023
Source dataset
uspto-grants-2015_09
Patent number
US09133171B2

Reaction notes

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