Triethylamine → O-ethyl S-propyl O-(4-nitroindan-1-on-7-yl) thiophosphate

HRID 2059182Notes

Reaction equation

HRID 2059182 reaction equation
[P:1](Cl)([S:6][CH2:7][CH2:8][CH3:9])([O:3][CH2:4][CH3:5])=[O:2].[N+:11]([C:14]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]2[C:15]=1[CH2:16][CH2:17][C:18]2=[O:24])([O-:13])=[O:12].C(N(CC)CC)C>C1(C)C=CC=CC=1>[P:1]([O:23][C:20]1[CH:21]=[CH:22][C:14]([N+:11]([O-:13])=[O:12])=[C:15]2[C:19]=1[C:18](=[O:24])[CH2:17][CH2:16]2)([S:6][CH2:7][CH2:8][CH3:9])([O:3][CH2:4][CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11745722O-Ethyl S-propyl chlorothiophosphateHCID 205459744-Nitro-7-hydroxyindan-1-one

Product 1

HCID 53891676O-ethyl S-propyl O-(4-nitroindan-1-on-7-yl) thiophosphate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

O-Ethyl S-propyl chlorothiophosphate (0.015 mole) dissolved in dry toluene (80) is charged into a glass reaction vessel equipped with a stirrer, thermometer and gas inlet tube. The solution is cooled to about 0° C. and a solution of 4-nitro-7-hydroxyindan-1-one (0.015 mole) and triethylamine (0.0175 mole) in toluene (20 ml) is slowly added with stirring. After the addition is completed the reaction mixture is allowed to warm to room temperature and stirring is continued for a period of about 8 hours. After this time the reaction mixture is filtered and the filtrate is washed with water. The washed solution is then dried and is stripped of solvent leaving a residue. This residue is chromatographed through a 200 ml clay column using ethyl acetate and hexane mixtures as the eluant. Ten separate fractions each containing increasing percentages of ethyl acetate are collected and analyzed by IR for the product. The appropriate fractions are then combined stripped of solvent and subjected to vacuum to yield the desired product, O-ethyl S-propyl O-(4-nitroindan-1-on-7-yl) thiophosphate.

Workup

  1. additionis charged into a glass reaction vessel
  2. customequipped with a stirrer
  3. additionAfter the addition
  4. temperatureto warm to room temperature
  5. stirringstirring
  6. filtrationAfter this time the reaction mixture is filtered
  7. washthe filtrate is washed with water
  8. customThe washed solution is then dried
  9. customleaving a residue
  10. customThis residue is chromatographed through a 200 ml clay column
  11. customTen separate fractions each containing
  12. temperatureincreasing percentages of ethyl acetate
  13. customare collected

Sources & evidence

ORD record
ord-6c78b1f1a5564db5a7664d0432075382
Source dataset
uspto-grants-1982_03
Patent number
US04322414

Reaction notes

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