Acetone → HCID 178436341, compound

HRID 483190Notes

Reaction equation

HRID 483190 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[N:10]#[C:11]Br.[CH2:13](N(CC)CC)C.[CH3:20][C:21]([CH3:23])=[O:22]>>[O-:22][C:4]#[N:3].[CH:4]([C:9]1[CH:23]=[CH:21][CH:20]=[CH:11][N:10]=1)=[CH:5][C:6]1[CH:8]=[CH:13][CH:1]=[CH:2][CH:7]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 79532,4,6-TrimethylpyridineHCID 8471TriethylamineHCID 10476Cyanogen Bromide

Product 1

HCID 178436341HCID 178436341, compound

Procedure

A portion of the reaction product of a 1 to 2 mole ratio of 2,4,6-trimethyl pyridine and p-hydroxy benzaldehyde (7.30 grams, 0.0443 moles of hydroxyl groups) from 1-A above and acetone (150 grams) were added to a 1-liter glass resin kettle and maintained under a nitrogen atmosphere. Stirring and cooling were both started and when the temperature of the slurry reached 0° C., cyanogen bromide was added (4.93 grams, 0.0466 mole). After five minutes (300 s), triethylamine (4.51 grams, 0.0466 mole) was added dropwise over a four minute (240 s) period and so as to maintain the reaction temperature between 0° and 4° C. The reaction was allowed to progress for an additional 30 minutes (1800 s) between reaction temperatures of -1° to 5° C. After this time, the reaction slurry was filtered. The recovered filtrate was added to 750 milliliters of deionized water producing a voluminous pale white colored precipitate. The precipitate was recovered by filtration, washed with 100 milliliters of deionized water and then dried under vacuum at 25° C. to a constant weight of 2.2 grams. The unreacted trimethyl pyridine and p-hydroxy benzaldehyde adduct as well as triethylamine hydrochloride were recovered from the filter (5.2 grams), as a pale white colored powder. Infrared spectrophotometric analysis of a potassium bromide pellet of the product revealed the presence of cyanate group absorbance (2225 cm-1 and 2260 cm-1) accompanied by a substantial absence of a hydroxy group absorbance (3300 cm-1). As expected, trans-unsaturation absorbance (970 cm-1) and aromatic carbon-oxygen absorbance (1250 cm-1) remained.

Workup

  1. temperaturemaintained under a nitrogen atmosphere
  2. temperaturecooling
  3. customreached 0° C.
  4. temperatureso as to maintain the reaction temperature between 0° and 4° C
  5. custom(1800 s) between reaction temperatures of -1° to 5° C
  6. filtrationAfter this time, the reaction slurry was filtered
  7. additionThe recovered filtrate was added to 750 milliliters of deionized water producing a voluminous pale white colored precipitate
  8. filtrationThe precipitate was recovered by filtration
  9. washwashed with 100 milliliters of deionized water
  10. customdried under vacuum at 25° C. to a constant weight of 2.2 grams
  11. customThe unreacted trimethyl pyridine and p-hydroxy benzaldehyde adduct as well as triethylamine hydrochloride were recovered from the
  12. filtrationfilter (5.2 grams)

Sources & evidence

ORD record
ord-1357d086291c4fc19ef7ba0e40ee6e50
Source dataset
uspto-grants-1986_03
Patent number
US04578439

Reaction notes

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