Tetrahydrofuran → HCID 57005319, compound

HRID 1262567Notes

Reaction equation

HRID 1262567 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)=[C:10]([S:16]([CH3:18])=[O:17])[CH:9]=[CH:8][CH:7]=3)[CH:3]=1.C(N(CC)CC)C.O1CCCC1.[P:31](=[O:51])(Cl)([S:40][C:41]1[CH:46]=[CH:45][C:44]([N+:47]([O-:49])=[O:48])=[CH:43][CH:42]=1)[O:32][C:33]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[P:31](=[O:51])([S:40][C:41]1[CH:46]=[CH:45][C:44]([N+:47]([O-:49])=[O:48])=[CH:43][CH:42]=1)([O:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[CH:5][C:6]3[C:11]([N:12]=2)=[C:10]([S:16]([CH3:18])=[O:17])[CH:9]=[CH:8][CH:7]=3)[CH:3]=1)[O:32][C:33]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 20456885HCID 20456885, compoundHCID 57296761HCID 57296761, compound

Product 1

HCID 57005319HCID 57005319, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2-Hydroxy-5-methylsulfinylacridine (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-(4-fluorophenyl) S-(4-nitrophenyl) phosphorochloridothioate (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-(4-fluorophenyl) O-(5-methylsulfinylacridin-2-yl) S-(4-nitrophenyl) phosphorothioate.

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-44642b120f1d4be5b17b7406a743377a
Source dataset
uspto-grants-1984_06
Patent number
US04452792

Reaction notes

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