Pyridine → HCID 14438699, compound

HRID 1762781Notes

Reaction equation

HRID 1762781 reaction equation
[N:1]([CH2:8][CH2:9][OH:10])([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4].N1C=CC=CC=1.Cl[C:18]([C:20]1[C:32]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25](=[C:33]([C:36]#[N:37])[C:34]#[N:35])[C:24]=2[CH:23]=[CH:22][CH:21]=1)=[O:19]>ClCCl>[C:36]([C:33]([C:34]#[N:35])=[C:25]1[C:24]2[CH:23]=[CH:22][CH:21]=[C:20]([C:18]([O:4][CH2:3][CH2:2][N:1]([CH2:8][CH2:9][OH:10])[CH2:5][CH2:6][OH:7])=[O:19])[C:32]=2[C:31]2[C:26]1=[CH:27][CH:28]=[CH:29][CH:30]=2)#[N:37]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7618TriethanolamineHCID 198332559-(Dicyanomethylidene)-9H-fluorene-4-carbonyl chloride

Product 1

HCID 14438699HCID 14438699, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 100.0 grams of triethanolamine and 58 milliliters of dry pyridine in 350 milliliters of dry 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 dry dichloromethane was added over a period of 1 hour. After addition, the reaction mixture was further stirred for another hour. The reaction mixture was washed several times with water to remove the excess amines and the corresponding hydrochloride salts, dried with anhydrous magnesium sulfate and filtered. Evaporation of the filtrate gave 5 grams of crude product. Purification by recrystallization from isopropanol afforded 4.5 grams of pure (1c), mp., 155.5°-156.5° C.

Workup

  1. additionAfter addition
  2. washThe reaction mixture was washed several times with water
  3. customto remove the excess amines
  4. dry with materialthe corresponding hydrochloride salts, dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customEvaporation of the filtrate
  7. customgave 5 grams of crude product
  8. customPurification
  9. customby recrystallization from isopropanol

Sources & evidence

ORD record
ord-9b8399d3cc134ac78069fbfb0fbd8d50
Source dataset
uspto-grants-1989_05
Patent number
US04835081

Reaction notes

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