Triethylamine → HCID 57269752, compound

HRID 1632217Notes

Reaction equation

HRID 1632217 reaction equation
[Cl:1][C:2]1[C:15]2[C:6](=[CH:7][C:8]3[C:13]([CH:14]=2)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:5]=[C:4]([OH:16])[CH:3]=1.C(N(CC)CC)C.[P:24](=[O:32])(Cl)([S:27][CH2:28][CH2:29][CH3:30])[O:25][CH3:26].C(OCC)(=O)C>C1(C)C=CC=CC=1>[P:24](=[O:32])([S:27][CH2:28][CH2:29][CH3:30])([O:16][C:4]1[CH:3]=[C:2]([Cl:1])[C:15]2[C:6](=[CH:7][C:8]3[C:13]([CH:14]=2)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:5]=1)[O:25][CH3:26]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 12917781Phosphorochloridothioic acid, O-methyl S-propyl esterHCID 20443614HCID 20443614, compound

Product 1

HCID 57269752HCID 57269752, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

4-Chloro-2-anthrol (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-methyl S-propyl 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-methyl O-(4-chloro-2-anthryl) S-propyl 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-e7b33939738a480ca4835e7315b39ad0
Source dataset
uspto-grants-1984_10
Patent number
US04474776

Reaction notes

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