Tetrahydrofuran → HCID 57323816, compound

HRID 1262560Notes

Reaction equation

HRID 1262560 reaction equation
[Br:1][C:2]1[CH:15]=[C:14]([OH:16])[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.[CH2:17](N(CC)CC)C.O1CCCC1.[P:29]([S:35][CH2:36][CH3:37])(=[S:34])(Cl)[O:30][CH2:31][CH3:32]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[P:29]([S:35][CH2:36][CH3:37])(=[S:34])([O:16][C:14]1[C:13]2[C:4](=[CH:5][C:6]3[C:11]([N:12]=2)=[CH:10][C:9]([CH3:17])=[CH:8][CH:7]=3)[CH:3]=[C:2]([Br:1])[CH:15]=1)[O:30][CH2:31][CH3:32]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13127437HCID 13127437, compoundHCID 20456884HCID 20456884, compound

Product 1

HCID 57323816HCID 57323816, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-4-hydroxyacridine (0.01 mole), triethylamine (0.01 mole), tetrahydrofuran (25 ml) and toluene (25 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The mixture is cooled to a temperature of about 0° C. and O,S-diethyl phosphorochloridodithioate (0.01 mole) dissolved in toluene (25 ml) is added with stirring over a period of about 30 minutes. After the addition is completed the reaction mixture is allowed to warm to room temperature and stirring is continued for a period of about 16 hours. After this time the reaction mixture is filtered to remove triethylamine hydrochloride. The filtrate is then washed with water, dried over anhydrous magnesium sulfate and stripped of solvents leaving a residue. This residue is subjected to flash chromatography using ethyl acetate as the eluant to yield the desired product O,S-diethyl O-(2-bromo-6-methylacridin-4-yl) phosphorodithioate.

Workup

  1. customequipped with a mechanical stirrer
  2. additionis added
  3. additionAfter the addition
  4. stirringstirring
  5. waitis continued for a period of about 16 hours
  6. filtrationAfter this time the reaction mixture is filtered
  7. customto remove triethylamine hydrochloride
  8. washThe filtrate is then washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customleaving a residue

Sources & evidence

ORD record
ord-ba25049d18f8410b9f4f07563bce2909
Source dataset
uspto-grants-1984_06
Patent number
US04452792

Reaction notes

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