Sodium Hydroxide → HCID 14699193, compound

HRID 359463Notes

Reaction equation

HRID 359463 reaction equation
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[CH:9][CH:10]=[O:11].[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:29]=[C:28]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)[CH2:27][C:22]3([CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:21]=2)=[CH:16][CH:15]=1.[OH-].[Na+]>C(#N)C>[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:29]=[C:28]([C:30]3[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=3)[CH2:27][C:22]3([CH2:23][CH2:24][CH2:25][CH2:26]3)[C:21]=2/[CH:8]=[CH:9]/[CH:10]=[O:11])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 791253-(Dimethylamino)-2-propenalHCID 14994096HCID 14994096, compound

Product 1

HCID 14699193HCID 14699193, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of phosphorus oxychloride (1.69 ml, 18.15 mmoles) in 50 ml of acetonitrile cooled in an ice bath was added 3-dimethylaminoacrolein (1.68 ml, 16.75 mmoles) dropwise over 3 minutes. The mixture was stirred for 5 minutes and a solution of 7.9-di-(4-fluorophenyl)-spiro[4.5]-deca-6,8-diene (4.5 g, 13.96 mmoles) in 150 ml of warm acetonitrile was added dropwise over 30 minutes. The mixture was stirred at room temperature for 16 hours and was then heated in an oil bath at 60° C. for 6 hours. The mixture was cooled and poured into 400 ml of cold 1N sodium hydroxide. The mixture was extracted with ether. The ether was washed with water and evaporated in vacuo.

Workup

  1. stirringThe mixture was stirred at room temperature for 16 hours
  2. temperatureThe mixture was cooled
  3. extractionThe mixture was extracted with ether
  4. washThe ether was washed with water
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-56d008bd3d0a4e0bb3d2898e6fa8c1d8
Source dataset
uspto-grants-1991_03
Patent number
US05001128

Reaction notes

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