Toluene → HCID 20456883, compound

HRID 1262557Notes

Reaction equation

HRID 1262557 reaction equation
[Cl:1][C:2]1C2[C:6](=NC3C(C=2)=CC=CC=3)[CH:5]=[CH:4][C:3]=1[OH:16].C([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])C.[P:24](=[O:33])(Cl)([S:28][CH2:29][CH2:30][CH3:31])[O:25][CH2:26][CH3:27].C(OCC)(=O)C.[C:40]1(C)[CH:45]=CC=[CH:42][CH:41]=1>>[P:24](=[O:33])([S:28][CH2:29][CH2:30][CH3:31])([O:16][C:3]1[C:2]([Cl:1])=[CH:21][C:20]2[C:5](=[CH:6][C:23]3[C:22]([N:19]=2)=[CH:42][CH:41]=[CH:40][CH:45]=3)[CH:4]=1)[O:25][CH2:26][CH3:27]

Participants

6

Reactant 5

HCID 1140TolueneHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 11745722O-Ethyl S-propyl chlorothiophosphateHCID 20456887Chloro-2-hydroxyacridine

Product 1

HCID 20456883HCID 20456883, compound

Procedure

The acridine prepared above and triethylamine (1.4 ml) are charged into a glass reaction vessel equipped with a stirrer and thermometer. To this is added a cooled solution (0° C.) of O-ethyl S-propyl phosphorochloridothioate (0.01 mole) in toluene (25 ml). The mixture is stirred with continued cooling for 1/2 hour and thereafter at room temperature overnight. After this time the reaction mixture is filtered to remove triethylamine hydrochloride and the filtrate is stripped of solvent in a rotary evaporator leaving a residue. This residue is subjected to flash chromatography using ethyl acetate as the eluant to yield the desired product.

Workup

  1. additionare charged into a glass reaction vessel
  2. customequipped with a stirrer
  3. temperaturewith continued cooling for 1/2 hour
  4. customat room temperature
  5. customovernight
  6. filtrationAfter this time the reaction mixture is filtered
  7. customto remove triethylamine hydrochloride
  8. customthe filtrate is stripped of solvent in a rotary evaporator
  9. customleaving a residue

Sources & evidence

ORD record
ord-e8aef86c731d4b54a9b7a945688cb5fd
Source dataset
uspto-grants-1984_06
Patent number
US04452792

Reaction notes

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