Chlorosulfonyl isocyanate → HCID 10535719, compound

HRID 1291950Notes

Reaction equation

HRID 1291950 reaction equation
ClS([N:5]=[C:6]=[O:7])(=O)=O.O[C:9]([CH3:19])([CH3:18])[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11]>C1(C)C=CC=CC=1>[C:6]([C:9]([CH3:19])([CH3:18])[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11])(=[O:7])[NH2:5]

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 819842-Hydroxy-2-methyl-1-phenylpropan-1-one

Product 1

HCID 10535719HCID 10535719, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of chlorosulfonyl isocyanate in toluene was added to a solution of 2-hydroxy-2-methyl propiophenone in anhydrous toluene at 0° C. The mixture was stirred at room temperature for 1.5 hours then the resulting precipitate was collected. The precipitate was taken up in dioxane, cooled to 0°, then triturated with water. Prior to extraction with ether the dioxane solution was stirred overnight at room temperature. Extracted ether phase was treated with aqueous sodium bicarbonate until neutral, dried over sodium sulfate, and concentrated to leave a clear colorless oil. Upon trituration with petroleum ether the oil crystallized to leave a white solid. After drying the solid, 2-carbamoyl-2-methyl propiophenone was obtained in 60% yield. This carbamate was heated at 180° C. under a weak vacuum to form the imine. The carbamate melted at 120° C., was stirred at 180° C. for 30-50 minutes, then solidified upon cooling. The crude product was recrystallized from benzene/cyclohexane to give a 73% yield of the desired product with mp. 106°-108.5° C. (lit. 111-111.5). The product was confirmed by NMR, MS, and IR analysis. ##STR15##

Workup

  1. customthe resulting precipitate was collected
  2. temperaturecooled to 0°
  3. customtriturated with water
  4. extractionPrior to extraction with ether the dioxane solution
  5. stirringwas stirred overnight at room temperature
  6. additionExtracted ether phase was treated with aqueous sodium bicarbonate until neutral,
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customto leave a clear colorless oil
  10. customUpon trituration with petroleum ether the oil crystallized
  11. customto leave a white solid
  12. customAfter drying the solid

Sources & evidence

ORD record
ord-c9cefcd64393492ca01e060a8bbeef91
Source dataset
uspto-grants-1998_05
Patent number
US05755991

Reaction notes

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