Dimethylformamide → HCID 20399003, compound

HRID 1981281Notes

Reaction equation

HRID 1981281 reaction equation
CN(C)C=O.[C:6]([C:8]1[C:13]([C:14]#[N:15])=[C:12]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:11]=[CH:10][C:9]=1[OH:21])#[N:7].C(=O)([O-])[O-].[K+].[K+].[CH2:28]([C:31]12[CH2:38][CH2:37][C:34]([CH2:39]Br)([CH2:35][CH2:36]1)[CH2:33][CH2:32]2)[CH2:29][CH3:30]>O>[C:6]([C:8]1[C:13]([C:14]#[N:15])=[C:12]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:11]=[CH:10][C:9]=1[O:21][CH2:39][C:34]12[CH2:35][CH2:36][C:31]([CH2:28][CH2:29][CH3:30])([CH2:38][CH2:37]1)[CH2:32][CH2:33]2)#[N:7]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 203989701-(Bromomethyl)-4-propylbicyclo[2.2.2]octaneHCID 203990393-Hydroxy-6-pentylbenzene-1,2-dicarbonitrile

Product 1

HCID 20399003HCID 20399003, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

50 ml of dimethylformamide were added to 0.04 mole of 2,3-dicyano-4-pentylphenol, 0.2 mole of potassium carbonate and 0.04 mole of 4-propyl-1-bicyclo(2,2,2)-octylmethyl bromide. The mixture was stirred at 80° C. for 48 hours. The mixture was then cooled to room temperature and poured into 200 ml of water and the organic phase was extracted. The organic extract was washed with water and dried over magnesium sulfate. After the solvent had been evaporated off, the crude product was recrystallized several times. The pure product has a high melting point of 133.1° C. and a negative DCA.

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. extractionthe organic phase was extracted
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried over magnesium sulfate
  6. customAfter the solvent had been evaporated off
  7. customthe crude product was recrystallized several times

Sources & evidence

ORD record
ord-6543fd1f774448baae67055298b1c141
Source dataset
uspto-grants-1985_04
Patent number
US04514317

Reaction notes

Loading…