Acetone → HCID 69992799, compound

HRID 481135Notes

Reaction equation

HRID 481135 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:18])[CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.CC(C)=O.[N:23]#[C:24]Cl.[CH2:26]([N:28](CC)CC)C>O>[O:1]([C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:18])[CH:9]=[CH:10][C:11]2[CH:12]=[CH:13][C:14]([O:17][C:24]#[N:23])=[CH:15][CH:16]=2)=[CH:4][CH:3]=1)[C:26]#[N:28]

Participants

6

Reactant 4

HCID 180AcetoneHCID 8471TriethylamineHCID 10477Cyanogen ChlorideHCID 134561HCID 134561, compound

Product 1

HCID 69992799HCID 69992799, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-10 °C

Procedure

10 g (41.5 mmol) of 1,3-bis-(4-hydroxyphenyl)-2-propen-1-one were initially charged in a double-walled reactor (250 ml) fitted with stirrer, thermometer, gas inlet tube and a metering pump for liquors. After addition of 110 ml of anhydrous acetone, the solution was cooled to −10° C. Over a period of 10 minutes, 5.63 g (91.5 mmol) of cyanogen chloride were then introduced initially, followed by the metered addition, with vigorous stirring, of 8.55 g (84.5 mmol) of triethylamine at a flow rate of approximately 0.4 ml/min, during which the temperature of the reaction mixture was kept below −10° C. at all times. The reaction mixture was then warmed to 20° C. and stirred at this temperature for 30 minutes. Over a period of 10 minutes, the reaction mixture was subsequently added with vigorous stirring to 200 ml of water which had been cooled to 5° C. beforehand. The suspension was then stirred for 30 minutes, slowly warmed to 15° C. and filtered. The filter cake was washed with water (2×30 ml) and dried in a vacuum drying cabinet at 20 mbar/50° C. for 20 hours. In this manner, 11.03 g (92%) of cyanate having a melting point of 171-173° C. were isolated.

Workup

  1. customfitted with stirrer
  2. customwas kept below −10° C. at all times
  3. temperatureThe reaction mixture was then warmed to 20° C.
  4. waitOver a period of 10 minutes
  5. additionthe reaction mixture was subsequently added
  6. temperaturehad been cooled to 5° C. beforehand
  7. stirringThe suspension was then stirred for 30 minutes
  8. temperatureslowly warmed to 15° C.
  9. filtrationfiltered
  10. washThe filter cake was washed with water (2×30 ml)
  11. customdried in a vacuum
  12. customdrying cabinet at 20 mbar/50° C. for 20 hours

Sources & evidence

ORD record
ord-619a0220b9604e8384a6d1c7ba192f97
Source dataset
uspto-grants-2003_11
Patent number
US06653497B1

Reaction notes

Loading…