Ethanol → HCID 53907215, compound

HRID 1613405Notes

Reaction equation

HRID 1613405 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[CH2:8]([OH:10])[CH3:9].[C:11]1([OH:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>C(Cl)Cl>[C:11]1([O:17][S:2](=[O:4])(=[O:3])[NH:5][C:6]([O:10][CH2:8][CH3:9])=[O:7])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 996PhenolHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 53907215HCID 53907215, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Chlorosulfonyl isocyanate (98%, 13.4 ml, 0.15 mole) was stirred in 40 ml of methylene chloride in an acetone-ice bath. Ethanol (8.8 ml, 0.15 mole) dissolved in 20 ml methylene chloride was added dropwise over 28 minutes. The reaction was stirred at room temperature for 15 minutes and then chilled in an ice bath. To the reaction was added a solution of phenol (11.3 g, 0.12 mole) and triethylamine (21 ml, 0.15 mole) in methylene chloride (20 ml) over 27 minutes. The reaction was stirred at ambient temperature for 4 hours and then extracted twice with dilute hydrochloric acid. The organic layer was dried over sodium sulfate and evaporated to 31 g oil. This oil was chromatographed on about 300 g silica gel eluted with 2% ethyl acetate/methylene chloride. The pure fractions were combined and concentrated to 15 g oil.

Workup

  1. additionwas added dropwise over 28 minutes
  2. temperaturechilled in an ice bath
  3. stirringThe reaction was stirred at ambient temperature for 4 hours
  4. extractionextracted twice with dilute hydrochloric acid
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customevaporated to 31 g oil
  7. customThis oil was chromatographed on about 300 g silica gel
  8. washeluted with 2% ethyl acetate/methylene chloride
  9. concentrationconcentrated to 15 g oil

Sources & evidence

ORD record
ord-e670bf266080445ab52035d55aaf58a2
Source dataset
uspto-grants-1993_03
Patent number
US05192785

Reaction notes

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