Tetrahydrofuran → HCID 13342910, compound

HRID 1262555Notes

Reaction equation

HRID 1262555 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[CH:5][C:6]3[C:11]([N:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1.C(N(CC)CC)C.O1CCCC1.[P:28](=[O:37])(Cl)([S:32][CH2:33][CH2:34][CH3:35])[O:29][CH2:30][CH3:31]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[P:28](=[O:37])([S:32][CH2:33][CH2:34][CH3:35])([O:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[CH:5][C:6]3[C:11]([N:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1)[O:29][CH2:30][CH3:31]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 315322-AcridinolHCID 11745722O-Ethyl S-propyl chlorothiophosphate

Product 1

HCID 13342910HCID 13342910, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

2-Hydroxyacridine (1.90 grams; 0.01 mole), triethylamine (1.01 grams; 0.01 mole), tetrahydrofuran (30 ml) and toluene (20 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The mixture was cooled to about 0° C. and O-ethyl S-propyl phosphorochloridothioate (2.01 grams; 0.01 mole) dissolved in toluene (23 ml) was added with stirring over a period of about 20 minutes. After the addition was completed stirring was continued for 3 hours allowing the mixture to warm up to room temperature. Stirring was continued overnight. After this time the reaction mixture was filtered to remove triethylamine hydrochloride. The filtrate was washed, treated with charcoal and stripped of solvent leaving yellow/green oil as the residue. This residue was subjected to flash chromatography using ethyl acetate as the eluant to yield the desired product O-ethyl O-acridin-2-yl S-propyl phosphorothioate as a yellow brown oil.

Workup

  1. customequipped with a mechanical stirrer
  2. additionwas added
  3. additionAfter the addition
  4. stirringwas completed stirring
  5. waitwas continued for 3 hours
  6. temperatureto warm up to room temperature
  7. stirringStirring
  8. waitwas continued overnight
  9. filtrationAfter this time the reaction mixture was filtered
  10. customto remove triethylamine hydrochloride
  11. washThe filtrate was washed
  12. additiontreated with charcoal
  13. customleaving yellow/green oil as the residue

Sources & evidence

ORD record
ord-aad120d2485043c880b8531b388e3ef9
Source dataset
uspto-grants-1984_06
Patent number
US04452792

Reaction notes

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