Ethyl Acetate → HCID 68884629, compound

HRID 2113895Notes

Reaction equation

HRID 2113895 reaction equation
Cl[S:2]([N:5]=[C:6]=O)(=[O:4])=[O:3].S(Cl)(=O)(=O)N.S(Cl)(Cl)(=O)=O.[CH3:18][O:19][C:20](=[O:34])[C:21]1[CH:26]=[CH:25][C:24]([NH:27]CC(OCC)=O)=[CH:23][CH:22]=1.[C:35]([O:38][CH2:39][CH3:40])(=[O:37])C>C(Cl)Cl.C(N(CC)CC)C.C(O)=O>[CH3:18][O:19][C:20](=[O:34])[C:21]1[CH:22]=[CH:23][C:24]([NH:27][S:2](=[O:3])(=[O:4])[NH:5][CH2:6][C:35]([O:38][CH2:39][CH3:40])=[O:37])=[CH:25][CH:26]=1

Participants

9

Reactant 5

HCID 8857Ethyl AcetateHCID 24499Chlorosulfamic acidHCID 24648Sulfuryl chlorideHCID 70918Chlorosulfonyl isocyanateHCID 21163315HCID 21163315, compound

Product 1

HCID 68884629HCID 68884629, compound

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolvent2×HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Procedure

A flame-dried flask was charged with chlorosulfonyl isocyanate. Anhydrous formic acid (96%) was added dropwise resulting in evolution of a gas. The solution solidified halfway through the addition of the formic acid and eventually turned to a cloudy liquid (the crude sulfamyl chloride). The solution was stirred at room temperature until no further gas evolution was observed. The sulfonyl chloride was diluted with 20 mL dry methylene chloride and added to a 0° C. solution of 101/triethyl amine in 20 mL methylene chloride. The reaction was stirred from 0° C. to room temperature over 2 hours (TLC showed approximately 50% starting material in 30% ethyl acetate/hexanes) and overnight at room temperature. The reaction showed mostly two spots by TLC (70:30 ethyl acetate:hexanes). The reaction was diluted with methylene chloride, washed with 10% HCl, dried over sodium sulfate, filtered, and concentrated to a light yellow oil. The crude mixture was purified by flash column by adsorbing onto silica and eluting with 20% ethyl acetate/hexanes to recover starting material and the white solid 102.

Workup

  1. customresulting in evolution of a gas
  2. washwashed with 10% HCl
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a light yellow oil
  6. customThe crude mixture was purified by flash column
  7. washeluting with 20% ethyl acetate/hexanes
  8. customto recover

Sources & evidence

ORD record
ord-0ed241579c4244afbeae8cf613059bb7
Source dataset
uspto-grants-2008_10
Patent number
US07432292B2

Reaction notes

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