Tetrahydrofuran → HCID 57231297, compound

HRID 1262566Notes

Reaction equation

HRID 1262566 reaction equation
[OH:1][C:2]1[CH:15]=[C:14]([C:16]#[N:17])[C:13]2[C:4](=[CH:5][C:6]3[C:11]([N:12]=2)=[CH:10][C:9]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:8][CH:7]=3)[CH:3]=1.C(N(CC)CC)C.O1CCCC1.[P:34](=[O:51])(Cl)([S:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[O:35][C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([Br:42])[CH:37]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[P:34](=[O:51])([S:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([O:1][C:2]1[CH:15]=[C:14]([C:16]#[N:17])[C:13]2[C:4](=[CH:5][C:6]3[C:11]([N:12]=2)=[CH:10][C:9]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:8][CH:7]=3)[CH:3]=1)[O:35][C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([Br:42])[CH:37]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 20456895HCID 20456895, compoundHCID 57043717HCID 57043717, compound

Product 1

HCID 57231297HCID 57231297, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2-Hydroxy-4-cyano-6-methylsulfonylacridine (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-(3-bromophenyl) S-phenyl 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 wasshed 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-(3-bromophenyl) O-(4-cyano-6-methylfulfonylacridin-2-yl) S-phenyl 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. dry with materialdried over anhydrous magnesium sulfate
  9. customleaving a residue

Sources & evidence

ORD record
ord-22a7e55c02594991a6caba82bec026b9
Source dataset
uspto-grants-1984_06
Patent number
US04452792

Reaction notes

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