Phloroglucinol → HCID 14438698, compound

HRID 1762780Notes

Reaction equation

HRID 1762780 reaction equation
[C:1]1([CH:9]=[C:7]([OH:8])[CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].N1C=CC=CC=1.Cl[C:17]([C:19]1[C:31]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24](=[C:32]([C:35]#[N:36])[C:33]#[N:34])[C:23]=2[CH:22]=[CH:21][CH:20]=1)=[O:18]>ClCCl>[C:35]([C:32]([C:33]#[N:34])=[C:24]1[C:23]2[CH:22]=[CH:21][CH:20]=[C:19]([C:17]([O:2][C:1]3[CH:9]=[C:7]([OH:8])[CH:6]=[C:4]([OH:5])[CH:3]=3)=[O:18])[C:31]=2[C:30]2[C:25]1=[CH:26][CH:27]=[CH:28][CH:29]=2)#[N:36]

Participants

5

Reactant 3

HCID 359PhloroglucinolHCID 1049PyridineHCID 198332559-(Dicyanomethylidene)-9H-fluorene-4-carbonyl chloride

Product 1

HCID 14438698HCID 14438698, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 30.0 grams of phloroglucinol and 70 milliliters of pyridine in 300 milliliters of dichloromethane was stirred at room temperature under a nitrogen atmosphere. A solution of 8.0 grams of (4-chloroformyl-9-fluorenylidene)malononitrile in 400 milliliters of dichloromethane was added over a period of 1 hour. After addition, the reaction mixture was further stirred for another hour. The mixture was washed three times with dilute aqueous HCl solution, twice with dilute aqueous NaHCO3 solution, and once with water. The solution was dried, filtered and evaporated under reduced pressure to give the crude product. Recrystallization from methanol afforded 6.1 grams of (1b), mp., 255.5°-257° C.

Workup

  1. additionAfter addition
  2. washThe mixture was washed three times with dilute aqueous HCl solution
  3. customThe solution was dried
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto give the crude product
  7. customRecrystallization from methanol

Sources & evidence

ORD record
ord-95c5a72060cc4d00a8d9ef8ae0eb6a00
Source dataset
uspto-grants-1989_05
Patent number
US04835081

Reaction notes

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