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Triethylamine → O-ethyl O-(2-anthryl) S-propyl phosphorothioate

HRID 1632216
Notes
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Reaction equation

HRID 1632216 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][C:2]=1[OH:15].C(N(CC)CC)C.[P:23](=[O:32])(Cl)([S:27][CH2:28][CH2:29][CH3:30])[O:24][CH2:25][CH3:26].C(OCC)(=O)C>C1(C)C=CC=CC=1>[P:23](=[O:32])([S:27][CH2:28][CH2:29][CH3:30])([O:15][C:2]1[CH:3]=[CH:4][C:5]2[C:14](=[CH:13][C:12]3[C:7]([CH:6]=2)=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:1]=1)[O:24][CH2:25][CH3:26]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 995032-AnthrolHCID 11745722O-Ethyl S-propyl chlorothiophosphate

Product 1

HCID 13339650O-ethyl O-(2-anthryl) S-propyl phosphorothioate

Reagents, catalysts & solvents 1

HCID 1140Toluene
Solvent
2×

Conditions

Temperature
0 °C

Procedure

2-Anthrol (3.0 grams; 0.015 mole), triethylamine (2.1 ml) and toluene (50 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The mixture was cooled to about 0° C. and O-ethyl S-propyl phosphorochloridothioate (3.01 grams; 0.015 mole) dissolved in toluene (38 ml) was added with stirring over a period of about 1/2 hour. After the addition was completed stirring was continued at room temperature overnight. After this time the reaction mixture was filtered to remove triethylamine hydrochloride and the filtrate stripped of solvent leaving solid residue. This residue was subjected to flash chromatography using ethyl acetate as the eluant to yield the desired product O-ethyl O-(2-anthryl) S-propyl phosphorothioate as a light tan solid melting at 79° to 83° C.

Workup

  1. customequipped with a mechanical stirrer
  2. additionwas added
  3. additionAfter the addition
  4. stirringwas completed stirring
  5. waitwas continued at room temperature overnight
  6. filtrationAfter this time the reaction mixture was filtered
  7. customto remove triethylamine hydrochloride
  8. customleaving solid residue

Sources & evidence

ORD record
ord-5bcafa2e160f425ba323e349694c32c5
Source dataset
uspto-grants-1984_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04474776

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes