Sodium Hydroxide → HCID 14699193, compound

HRID 1200134Notes

Reaction equation

HRID 1200134 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. The residue was triturated with 17.5 ml of boiling hexane and was filtered. The filtrate, upon cooling in the freezer overnight, deposited 2.7 g of product having an m.p. of 120°-4° C.

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
  6. customThe residue was triturated with 17.5 ml of boiling hexane
  7. filtrationwas filtered
  8. temperatureThe filtrate, upon cooling in the freezer overnight

Sources & evidence

ORD record
ord-5626fc67dbf84ceaa6043805208cb3f8
Source dataset
uspto-grants-1990_02
Patent number
US04904691

Reaction notes

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